No renderable structure data available
C1=CC(=CC=C1CC(=O)NN)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-(4-fluorophenyl)acetohydrazide |
|---|---|
| IUPAC Name | — |
| CAS Number | 34547-28-9 |
| Database ID | 3771612 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-(4-fluorophenyl)acetohydrazide (CAS 34547-28-9) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 3771612
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f7b6fc78d0e24b64a8d4b8adee34515bConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(benzyloxy)-N,9,9-trimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carbothioamide (0.1 g, 0.278 mmol, 1.0 equiv) in acetonitrile (0.9 mL) under a nitrogen atmosphere, was added MeI (0.070 mL, 1.11 mmol, 4 equiv). The reaction was heated at 50° C. (oil bath) for 45 min. The reaction was then cooled to ambient temperature and concentrated in vacuo. 2-(4-Fluorophenyl)acetohydrazide (0.14 g, 0.84 mmol, 3 equiv) was then added to the residue followed by DMF (2 mL) and the slurry was heated at 140° C. (oil bath). After stirring 16 h, the reaction was cooled to ambient temperature and concentrated in vacuo. The residue was added to a saturated aqueous solution of NaHCO3 and extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo. The crude product was treated with DMF (˜1.5 mL). After trying to dissolve material, the insoluble portion was filtered and washed with methanol to provide the title compound (0.024 g, 22% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.21 (dd, J=8.81, 5.29 Hz, 2H), 7.03 (t, J=8.69 Hz, 2H), 4.24 (s, 2H), 4.04 (q, J=2.77 Hz, 4H), 3.93 (s, 3H), 1.57 (s, 6H); LCMS (ES+, (M+H)+) m/z 386.22. The reaction was then cooled to ambient temperature concentrated in vacuo the slurry was heated at 140° C. (oil bath) the reaction was cooled to ambient temperature concentrated in vacuo The residue was added to a saturated aqueous solution of NaHCO3 extracted with CH2Cl2 (×3) The combined CH2Cl2 extracts were dried (Na2SO4) concentrated in vacuo The crude product was treated with DMF (˜1.5 mL) to dissolve material the insoluble portion was filtered washed with methanol
Source ID: ord-9cb1be685e28446895eda5b47be84002Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a slurry of 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carbothioamide (0.04 g, 0.116 mmol, 1.0 equiv) in acetonitrile (1.2 mL) under a nitrogen atmosphere, was added MeI (0.011 mL, 0.174 mmol, 1.5 equiv). The reaction was heated at 50° C. (oil bath) for 1 h. The reaction was then cooled to ambient temperature and concentrated in vacuo. 2-(4-Fluorophenyl)acetohydrazide (0.058 g, 0.35 mmol, 3 equiv) was then added to the residue followed by methanol (1 mL) and the slurry was heated at 70° C. (oil bath). After stirring 1 h, the reaction was cooled to ambient temperature and concentrated in vacuo. DMF (1 mL) was added to the residue and the solution was heated at 150° C. (oil bath) for 3.5 h. The reaction was then cooled to ambient temperature and stirred 3 d. The reaction was heated at 140° C. (oil bath) for 2 h. The reaction was cooled to ambient temperature and concentrated in vacuo. The residue was added to a saturated aqueous solution of NaHCO3 and extracted with CH2Cl2 (×2). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo. The crude product was purified by reverse phase preparatory HPLC to provide the title compound (0.021 g, 49% yield) as a gray solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.99 (s, 2H), 7.21-7.39 (m, 2H), 7.00 (t, J=8.69 Hz, 2H), 4.17 (s, 2H), 4.05 (s, 4H), 1.62 (s, 6H); LCMS (ES+, (M+H)+) m/z 372.16. The reaction was then cooled to ambient temperature concentrated in vacuo the slurry was heated at 70° C. (oil bath) the reaction was cooled to ambient temperature concentrated in vacuo DMF (1 mL) was added to the residue the solution was heated at 150° C. (oil bath) for 3.5 h The reaction was then cooled to ambient temperature stirred 3 d The reaction was heated at 140° C. (oil bath) for 2 h The reaction was cooled to ambient temperature concentrated in vacuo The residue was added to a saturated aqueous solution of NaHCO3 extracted with CH2Cl2 (×2) The combined CH2Cl2 extracts were dried (Na2SO4) concentrated in vacuo The crude product was purified by reverse phase preparatory HPLC
Source ID: ord-b5fba06d87d6410c86373aa899c09f23Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of hydrazine (0.46 mL, 14.49 mmol, 2.5 equiv) in CH2Cl2 (29 mL) was added slowly over 30 sec 2-(4-fluorophenyl)acetyl chloride (0.79 mL, 5.79 mmol, 1.0 equiv). Slight warming of the mixture and white precipitate were observed. After stirring 45 min, the mixture was poured into a saturated aqueous solution of NaHCO3, layered with CH2Cl2 forming a thick emulsion. This emulsion was filtered through a medium glass frit to give a biphasic homogenous solution. This was extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo to provide the title compound (1.22 g, 124% yield) as a white solid. Source of extra mass is unclear as product is of high purity. Extra mass may reflect a measuring error of the acid chloride. 1H NMR (400 MHz, CDCl3) δ ppm 7.19-7.24 (m, 2H), 6.99-7.07 (m, 2H), 6.60 (s, 1H), 3.85 (d, J=2.01 Hz, 2H), 3.52 (s, 2H); LCMS (ES+, (M+H)+) m/z 169.22. Slight warming of the mixture and white precipitate This emulsion was filtered through a medium glass frit to give a biphasic homogenous solution This was extracted with CH2Cl2 (×3) The combined CH2Cl2 extracts were dried (Na2SO4) concentrated in vacuo
Source ID: ord-c1afdcd9b449437f87f5442ff16a323fConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(benzyloxy)-N,9,9-trimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carbothioamide (0.1 g, 0.278 mmol, 1.0 equiv) in acetonitrile (0.9 mL) under a nitrogen atmosphere, was added MeI (0.070 mL, 1.11 mmol, 4 equiv). The reaction was heated at 50° C. (oil bath) for 45 min. The reaction was then cooled to ambient temperature and concentrated in vacuo. 2-(4-Fluorophenyl)acetohydrazide (0.14 g, 0.84 mmol, 3 equiv) was then added to the residue followed by DMF (2 mL) and the slurry was heated at 140° C. (oil bath). After stirring 16 h, the reaction was cooled to ambient temperature and concentrated in vacuo. The residue was added to a saturated aqueous solution of NaHCO3 and extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo. The crude product was treated with DMF (˜1.5 mL). After trying to dissolve material, the insoluble portion was filtered and washed with methanol to provide the title compound (0.024 g, 22% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.21 (dd, J=8.81, 5.29 Hz, 2H), 7.03 (t, J=8.69 Hz, 2H), 4.24 (s, 2H), 4.04 (q, J=2.77 Hz, 4H), 3.93 (s, 3H), 1.57 (s, 6H); LCMS (ES+, (M+H)+) m/z 386.22. The reaction was then cooled to ambient temperature concentrated in vacuo the slurry was heated at 140° C. (oil bath) the reaction was cooled to ambient temperature concentrated in vacuo The residue was added to a saturated aqueous solution of NaHCO3 extracted with CH2Cl2 (×3) The combined CH2Cl2 extracts were dried (Na2SO4) concentrated in vacuo The crude product was treated with DMF (˜1.5 mL) to dissolve material the insoluble portion was filtered washed with methanol
Source ID: ord-9cb1be685e28446895eda5b47be84002Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a slurry of 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carbothioamide (0.04 g, 0.116 mmol, 1.0 equiv) in acetonitrile (1.2 mL) under a nitrogen atmosphere, was added MeI (0.011 mL, 0.174 mmol, 1.5 equiv). The reaction was heated at 50° C. (oil bath) for 1 h. The reaction was then cooled to ambient temperature and concentrated in vacuo. 2-(4-Fluorophenyl)acetohydrazide (0.058 g, 0.35 mmol, 3 equiv) was then added to the residue followed by methanol (1 mL) and the slurry was heated at 70° C. (oil bath). After stirring 1 h, the reaction was cooled to ambient temperature and concentrated in vacuo. DMF (1 mL) was added to the residue and the solution was heated at 150° C. (oil bath) for 3.5 h. The reaction was then cooled to ambient temperature and stirred 3 d. The reaction was heated at 140° C. (oil bath) for 2 h. The reaction was cooled to ambient temperature and concentrated in vacuo. The residue was added to a saturated aqueous solution of NaHCO3 and extracted with CH2Cl2 (×2). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo. The crude product was purified by reverse phase preparatory HPLC to provide the title compound (0.021 g, 49% yield) as a gray solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.99 (s, 2H), 7.21-7.39 (m, 2H), 7.00 (t, J=8.69 Hz, 2H), 4.17 (s, 2H), 4.05 (s, 4H), 1.62 (s, 6H); LCMS (ES+, (M+H)+) m/z 372.16. The reaction was then cooled to ambient temperature concentrated in vacuo the slurry was heated at 70° C. (oil bath) the reaction was cooled to ambient temperature concentrated in vacuo DMF (1 mL) was added to the residue the solution was heated at 150° C. (oil bath) for 3.5 h The reaction was then cooled to ambient temperature stirred 3 d The reaction was heated at 140° C. (oil bath) for 2 h The reaction was cooled to ambient temperature concentrated in vacuo The residue was added to a saturated aqueous solution of NaHCO3 extracted with CH2Cl2 (×2) The combined CH2Cl2 extracts were dried (Na2SO4) concentrated in vacuo The crude product was purified by reverse phase preparatory HPLC
Source ID: ord-b5fba06d87d6410c86373aa899c09f23Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of hydrazine (0.46 mL, 14.49 mmol, 2.5 equiv) in CH2Cl2 (29 mL) was added slowly over 30 sec 2-(4-fluorophenyl)acetyl chloride (0.79 mL, 5.79 mmol, 1.0 equiv). Slight warming of the mixture and white precipitate were observed. After stirring 45 min, the mixture was poured into a saturated aqueous solution of NaHCO3, layered with CH2Cl2 forming a thick emulsion. This emulsion was filtered through a medium glass frit to give a biphasic homogenous solution. This was extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo to provide the title compound (1.22 g, 124% yield) as a white solid. Source of extra mass is unclear as product is of high purity. Extra mass may reflect a measuring error of the acid chloride. 1H NMR (400 MHz, CDCl3) δ ppm 7.19-7.24 (m, 2H), 6.99-7.07 (m, 2H), 6.60 (s, 1H), 3.85 (d, J=2.01 Hz, 2H), 3.52 (s, 2H); LCMS (ES+, (M+H)+) m/z 169.22. Slight warming of the mixture and white precipitate This emulsion was filtered through a medium glass frit to give a biphasic homogenous solution This was extracted with CH2Cl2 (×3) The combined CH2Cl2 extracts were dried (Na2SO4) concentrated in vacuo
Source ID: ord-c1afdcd9b449437f87f5442ff16a323fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of hydrazine (0.46 mL, 14.49 mmol, 2.5 equiv) in CH2Cl2 (29 mL) was added slowly over 30 sec 2-(4-fluorophenyl)acetyl chloride (0.79 mL, 5.79 mmol, 1.0 equiv). Slight warming of the mixture and white precipitate were observed. After stirring 45 min, the mixture was poured into a saturated aqueous solution of NaHCO3, layered with CH2Cl2 forming a thick emulsion. This emulsion was filtered through a medium glass frit to give a biphasic homogenous solution. This was extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo to provide the title compound (1.22 g, 124% yield) as a white solid. Source of extra mass is unclear as product is of high purity. Extra mass may reflect a measuring error of the acid chloride. 1H NMR (400 MHz, CDCl3) δ ppm 7.19-7.24 (m, 2H), 6.99-7.07 (m, 2H), 6.60 (s, 1H), 3.85 (d, J=2.01 Hz, 2H), 3.52 (s, 2H); LCMS (ES+, (M+H)+) m/z 169.22. Slight warming of the mixture and white precipitate This emulsion was filtered through a medium glass frit to give a biphasic homogenous solution This was extracted with CH2Cl2 (×3) The combined CH2Cl2 extracts were dried (Na2SO4) concentrated in vacuo
Source ID: ord-c1afdcd9b449437f87f5442ff16a323fConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f7b6fc78d0e24b64a8d4b8adee34515bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared as described in Example 17 from 4-fluorophenylacetic acid hydrazide (1.04 mmol) and 3-chloro-6-thiophen-2-yl-pyridazine (0.52 mmol) as a pale beige solid. 1H NMR (CD3OD) δ 8.19 (1H, d, J=9.9 Hz), 7.93 (1H, dd, J=3.8 Hz, 0.9 Hz), 7.90 (1H, d, J=9.9 Hz), 7.75 (1H, dd, J=5.0 Hz, 1.0 Hz), 7.50 (2H, dd, J=9.0 Hz, 5.3 Hz), 7.24 (1H, dd, J=5.3 Hz, 3.8 Hz), 7.06 (2H, t, J=8.8 Hz), 4.59 (2H, s). ESI-MS (m/z): Calcd for C16H11FN4S: 310.1; found 311.2 (M+H).
Source ID: ord-0e5d081ebfa24f248b6c0ed627781d71Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared in analogy to example 71c) starting with [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (200 mg, 0.76 mmol) and (4-fluoro-phenyl)-acetic acid hydrazide (141 mg, 0.76 mmol). Obtained as a greyish solid (21 mg, 7%).
Source ID: ord-24ac314a1d3844eab96069fca66a33dfConditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Solid BrCN 13.37 g (130 mmol, 1.1 eq.) was added in one portion into ice-cooled slurry of (4-Fluoro-phenyl)-acetic acid hydrazide (19.85 g, 118 mmol) and KHCO3 14.77 g (147.5 mmol, 1.25 eq.) in MeOH (150 mL) in a 1L flask. (Followed by MeOH 10 mL to wash the funnel). The mixture was stirred on ice bath at 0-5° C. for 2 hours in a loose-capped flask, then the bath allowed to melt gradually and then the mixture was stirred at 5 to 20° C. overnight (17 hrs). The reaction mixture was diluted with water (200 mL), stirred for 1 hour in an open flask, then cooled on ice bath. The precipitate was collected by filtration, washed with water and dried on highvac. [1st fraction]The supernatants were concentrated on rotavap form warm (40° C.) water bath to remove all MeOH and some water. The obtained slurry was cooled to room temperature, the precipitate was collected by filtration, washed with water and dried on highvac. [2nd fraction]. Combined yield: 20.836 g (91.5%) of a white crystalline solid. to wash the funnel) the mixture was stirred at 5 to 20° C. overnight (17 hrs) The reaction mixture was diluted with water (200 mL) stirred for 1 hour in an open flask cooled on ice bath The precipitate was collected by filtration washed with water dried on highvac [1st fraction]The supernatants were concentrated on rotavap form warm (40° C.) water bath to remove all MeOH The obtained slurry was cooled to room temperature the precipitate was collected by filtration washed with water dried on highvac
Source ID: ord-090a6af3306d4c7c9c294f3515cdf504PubChem References
These sources are listed in the compound's public database record.
Request a Quote
Send the required specification, quantity, destination and intended use. The CATO team will review availability and respond.