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CC(C1=CC(=CC=C1)N)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1-(3-aminophenyl)ethanol |
|---|---|
| IUPAC Name | — |
| CAS Number | 201939-72-2 |
| Database ID | 222461 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1-(3-aminophenyl)ethanol (CAS 201939-72-2) 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 222461
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-0a876747e0a04a5a961cd5798b46cec9Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1c811752b60c4bbe867bd78be7eef7e4Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-fd7d356792154107b8758fb1aab5527dConditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-[2,4-dichloro-3-(2-methanesulfonyl-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-phenyl]-3-trifluoromethyl-benzamide (20 mg, 0.035 mmol) and 3-(1-hydroxyethyl)-aniline (50 mg, 0.364 mmol) is heated at 120° C. for ten minutes. The mixture is diluted with EtOAc and washed with saturated K2CO3, brine and water. The organic layer is dried, filtered and concentrated to give crude product, which is purified by prep-HPLC to give N-(2,4-dichloro-3-{2-[3-(1-hydroxy-ethyl)-phenylamino]-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}-phenyl)-3-trifluoromethyl-benzamide as a white solid. (17.9 mg, 81.4%). 1H NMR (CD3OD): δ 10.50 (s, 1H), 8.57 (d, 1H), 8.52 (s, 1H), 8.41 (s, 1H), 8.19 (s, 1H), 8.06 (d, 1H), 7.92 (s, 1H), 7.86 (d, 1H), 7.68 (t, 1H), 7.59 (d, 1H), 7.56 (s, 1H), 7.52 (d, 1H), 7.41 (t, 1H), 7.21 (s, 1H), 7.20 (d, 1H), 4.98 (q, 1H), 3.83 (s, 3H), 1.54 (d, 2H); MS m/z 629.10 (M+1). washed with saturated K2CO3, brine and water The organic layer is dried filtered concentrated to give crude product, which is purified by prep-HPLC
Source ID: ord-175525bb649c45499ac7b397c8d0d5a2Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-[2,4-dichloro-3-(2-methanesulfonyl-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-phenyl]-3-trifluoromethyl-benzamide (20 mg, 0.035 mmol) and 3-(1-hydroxyethyl)-aniline (50 mg, 0.364 mmol) is heated at 120° C. for ten minutes. The mixture is diluted with EtOAc and washed with saturated K2CO3, brine and water. The organic layer is dried, filtered and concentrated to give crude product, which is purified by prep-HPLC to give N-(2,4-dichloro-3-{2-[3-(1-hydroxy-ethyl)-phenylamino]-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}-phenyl)-3-trifluoromethyl-benzamide as a white solid. (17.9 mg, 81.4%). 1H NMR (CD3OD): δ 10.50 (s, 1H), 8.57 (d, 1H), 8.52 (s, 1H), 8.41 (s, 1H), 8.19 (s, 1H), 8.06 (d, 1H), 7.92 (s, 1H), 7.86 (d, 1H), 7.68 (t, 1H), 7.59 (d, 1H), 7.56 (s, 1H), 7.52 (d, 1H), 7.41 (t, 1H), 7.21 (s, 1H), 7.20 (d, 1H), 4.98 (q, 1H), 3.83 (s, 3H), 1.54 (d, 2H); MS m/z 629.10 (M+1). washed with saturated K2CO3, brine and water The organic layer is dried filtered concentrated to give crude product, which is purified by prep-HPLC
Source ID: ord-175525bb649c45499ac7b397c8d0d5a2Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-(2-Methanesulfonyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid dimethylamide (19.8 mg, 0.057 mmol), 1-(3-aminophenyl)ethanol (11.7 mg, 0.085 mmol) and trifluoroacetic acid (6.5 uL, 0.085 mmol) were combined in DMSO (0.5 M) and the mixture was heated in a capped vial at 100° C. for 16 hours. The dark solution was diluted with DMSO and purified by preparative LC. 5-{2-[3-(1-Hydroxyethyl)-phenylamino]-pyrimidin-4-yl}-thiophene-2-sulfonic acid dimethylamide (14.4 mg, 62.6%) was obtained as a brown solid after lyophilization. 1H NMR (500 MHz, DMSO-d6) δ 1.35 (d, J=6 Hz, 3H), 2.70 (s, 6H), 4.70 (m, 1H), 5.12 (d, J=4 Hz, 1H), 6.97 (br d, J=7 Hz, 1H), 7.24 (t, J=7.5 Hz, 1H), 7.46 (d, J=5.5 Hz, 1H), 7.49 (br d, J=6.5 Hz, 1H), 7.71 (d, J=4 Hz, 1H), 7.91 (br s, 1H), 8.12 (d, J=4 Hz, 1H), 8.58 (d, J=5.0 Hz, 1H), 9.75 (s, 1H). MS: m/z 405 (M+H+). purified by preparative LC
Source ID: ord-f354dbe24c414abdb67940f570fdaf2bConditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (150 mg, 351 μmol), 1-(3-aminophenyl)ethanol (72.2 mg, 526 μmol), xantphos (60.9 mg, 105 μmol), Pd2(dba)3 (32.1 mg, 35.1 μmol) and cesium carbonate (229 mg, 702 μmol) in dioxane (2 mL) was heated in a microwave at 150° C. for 20 min. The mixture was cooled then filtered through a pad of celite. The filtrate was concentrated in vacuo then purified by chromatography (silica, 40-70% ethyl acetate in hexanes) to give N-tert-butyl-2-(3-(1-hydroxyethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (143 mg, 148 μmol, 42%) as a yellow solid. (EI/CI) m/z: 519.3 [M+H]. The mixture was cooled then filtered through a pad of celite The filtrate was concentrated in vacuo then purified by chromatography (silica, 40-70% ethyl acetate in hexanes)
Source ID: ord-e4f44e636f614bf0955b40a0d9f41aa8Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-[2,4-dichloro-3-(2-methanesulfonyl-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-phenyl]-3-trifluoromethyl-benzamide (20 mg, 0.035 mmol) and 3-(1-hydroxyethyl)-aniline (50 mg, 0.364 mmol) is heated at 120° C. for ten minutes. The mixture is diluted with EtOAc and washed with saturated K2CO3, brine and water. The organic layer is dried, filtered and concentrated to give crude product, which is purified by prep-HPLC to give N-(2,4-dichloro-3-{2-[3-(1-hydroxy-ethyl)-phenylamino]-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}-phenyl)-3-trifluoromethyl-benzamide as a white solid. (17.9 mg, 81.4%). 1H NMR (CD3OD): δ 10.50 (s, 1H), 8.57 (d, 1H), 8.52 (s, 1H), 8.41 (s, 1H), 8.19 (s, 1H), 8.06 (d, 1H), 7.92 (s, 1H), 7.86 (d, 1H), 7.68 (t, 1H), 7.59 (d, 1H), 7.56 (s, 1H), 7.52 (d, 1H), 7.41 (t, 1H), 7.21 (s, 1H), 7.20 (d, 1H), 4.98 (q, 1H), 3.83 (s, 3H), 1.54 (d, 2H); MS m/z 629.10 (M+1). washed with saturated K2CO3, brine and water The organic layer is dried filtered concentrated to give crude product, which is purified by prep-HPLC
Source ID: ord-175525bb649c45499ac7b397c8d0d5a2Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0a876747e0a04a5a961cd5798b46cec9Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1c811752b60c4bbe867bd78be7eef7e4Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-fd7d356792154107b8758fb1aab5527dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure of Example I there was charged m-nitroacetophenone (33.0 g. 0.20 mole, 99% purity), water (300 ml.), and Raney nickel (14.8 g. (wet), Grace No. 4200) under 300 psi to 250 psi hydrogen. After 21/2 hours, work-up, by complete evaporation of the filtered hydrogenate, yielded 26.7 g. (97% yield) of m-amino-α-methylbenzyl alcohol which was 99.3% pure by GLC. After 21/2 hours, work-up, by complete evaporation of the filtered hydrogenate yielded 26.7 g
Source ID: ord-528561af91c94c3fbe6fff1bd94513cePubChem References
These sources are listed in the compound's public database record.
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