No renderable structure data available
C1C(=O)NC2=C(O1)C=CC(=C2)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 6-fluoro-4H-1,4-benzoxazin-3-one |
|---|---|
| IUPAC Name | — |
| CAS Number | 398-63-0 |
| Database ID | 302897 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
6-fluoro-4H-1,4-benzoxazin-3-one (CAS 398-63-0) 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 302897
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-19e64c99c8ad4b7a9e81175bce1aef00Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a150e88224584221a6332381dd0412dbConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-19e64c99c8ad4b7a9e81175bce1aef00Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-Fluoro-4H-benzo[1,4]oxazin-3-one (8173MF55b) (0.090 g, 0.54 mmol), Cs2CO3 (0.263 g, 0.81 mmol) and 3-chloro-1-iodopropane (0.121 g, 0.59 mmol) were mixed according to GP5. CC (SiO2; Heptane/EtOAc 10:1-5) gave the title compound (8173MF55b) (0.102 g, 78%). 1HNMR(CDCl3) δ 6.95-6.91 (m, 1H), 6.82-6.78 (m, 11H), 6.72-6.67 (m, 1H), 4.57 (s, 1H), 4.05 (t, J=7.2 Hz, 2H), 3.62 (t, J=6.2 Hz, 2H), 2.19-2.11 (m, 2H); 13CNMR(CDCl3) δ 164.6, 158.6 (d, J=240.7 Hz), 141.5 (d, J=2.3 Hz), 129.6 (d, J=10.5 Hz), 118.0 (d, J=9.3 Hz), 110.0 (d, J=23.1 Hz), 102.7 (d, J=28.8 Hz), 67.8, 42.3, 39.3, 30.0.
Source ID: ord-263ac271c3f0478fad0b660f167a8edaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 46 g of ethyl 4-fluoro-2-nitrophenoxyacetate, prepared in Example 18, in 500 ml of methanol is hydrogenated under atmospheric pressure in the presence of Raney nickel. After absorption of the theoretical quantity of hydrogen, the catalyst is filtered off, the solution is concentrated in vacuo and the residue is taken up in either, from which it crystallizes. The crystals formed are filtered off, washed with ether and dried. 28 g of 6-fluoro-2H-1,4-benzoxazin-3(4H)-one are thus obtained in the form of crystals of melting point 206°-207° C. After absorption of the theoretical quantity of hydrogen the catalyst is filtered off the solution is concentrated in vacuo crystallizes The crystals formed are filtered off washed with ether dried
Source ID: ord-5143396895a348108eed13b8051e5381Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a150e88224584221a6332381dd0412dbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: LiAlH4 (14.7 mmol, 1 M solution in THF) is added to a solution of 6-fluoro-4H-benzo[1,4]oxazin-3-one (1.23 g, 7.35 mmol) in THF at rt and heated to reflux for 2 hrs. The reaction mixture is quenched with a few drops of water followed by slow addition of ethyl acetate (10 mL). The solid is filtered off, and washed with EtOAc. The filtrate is concentrated in vacuo to afford 6-fluoro-3,4-dihydro-2H-benzo[1,4]oxazine (1 g). MS: 154 (M+H). heated to reflux for 2 hrs The reaction mixture is quenched with a few drops of water followed by slow addition of ethyl acetate (10 mL) The solid is filtered off washed with EtOAc The filtrate is concentrated in vacuo
Source ID: ord-8c9837da7ca04330b98e3a21e361d230Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: LiAlH4 (14.7 mmol, 1 M solution in THF) is added to a solution of 6-fluoro-4H-benzo[1,4]oxazin-3-one (1.23 g, 7.35 mmol) in THF at rt and heated to reflux for 2 hrs. The reaction mixture is quenched with a few drops of water followed by slow addition of ethyl acetate (10 mL). The solid is filtered off, and washed with EtOAc. The filtrate is concentrated in vacuo to afford 6-fluoro-3,4-dihydro-2H-benzo[1,4]oxazine (1 g). MS: 154 (M+H). heated to reflux for 2 hrs The reaction mixture is quenched with a few drops of water followed by slow addition of ethyl acetate (10 mL) The solid is filtered off washed with EtOAc The filtrate is concentrated in vacuo
Source ID: ord-8c9837da7ca04330b98e3a21e361d230Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-Fluoro-4H-benzo[1,4]oxazin-3-one (95MF88) (2.54 g, 15.2 mmol), (R)-3-bromo-2-methylpropoxy-tert-butyldimethylsilane (4.07 g, 15.2 mmol) and Cs2CO3 (12.38 g, 38 mmol) were mixed according to GP7. CC (SiO2; Heptane/EtOAc 9:1) gave the title compound (111MF01) (4.09 g, 76%). 1H NMR (CDCl3) δ 6.93-6.87 (m, 1H), 6.92-6.88 (m, 1H), 6.68-6.63 (m, 1H), 4.56 (m, 2H), 4.01 (m, 1H), 3.78 (m, 1H), 3.58 (m, 1H), 3.45 (m, 1H), 2.11 (m, 1H), 0.92 (s, 12H), 0.06 (d, J=0.8 Hz, 6H); 13C NMR (CDCl3) δ 164.8, 158.5 (d, J=239.9 Hz), 141.6 (d, J=2.7 Hz), 130.1 (d, J=10.7 Hz), 117.6 (d, J=9.3 Hz), 109.6 (d, J=23.1 Hz), 103.6 (d, J=28.8 Hz), 67.8, 65.9, 44.2, 34.5, 26.0, 18.4, 14.9, −5.4, −5.4.
Source ID: ord-e433384d55e4452591d6881c3765f11eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-Fluoro-4H-benzo[1,4]oxazin-3-one (8173MF55b) (0.090 g, 0.54 mmol), Cs2CO3 (0.263 g, 0.81 mmol) and 3-chloro-1-iodopropane (0.121 g, 0.59 mmol) were mixed according to GP5. CC (SiO2; Heptane/EtOAc 10:1-5) gave the title compound (8173MF55b) (0.102 g, 78%). 1HNMR(CDCl3) δ 6.95-6.91 (m, 1H), 6.82-6.78 (m, 1H), 6.72-6.67 (m, 1H), 4.57 (s, 1H), 4.05 (t, J=7.2 Hz, 2H), 3.62 (t, J=6.2 Hz, 2H), 2.19-2.11 (m, 2H); 13CNMR(CDCl3) δ 164.6, 158.6 (d, J=240.7 Hz), 141.5 (d, J=2.3 Hz), 129.6 (d, J=10.5 Hz), 118.0 (d, J=9.3 Hz), 110.0 (d, J=23.1 Hz), 102.7 (d, J=28.8 Hz), 67.8, 42.3, 39.3, 30.0.
Source ID: ord-9467e352ac3547d799fac6da0ec73237Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-Fluoro-4H-benzo[1,4]oxazin-3-one (95MF88) (2.54 g, 15.2 mmol), (R)-3-bromo-2-methylpropoxy-tert-butyldimethylsilane (4.07 g, 15.2 mmol) and Cs2CO3 (12.38 g, 38 mmol) were mixed according to GP7. CC (SiO2; Heptane/EtOAc 9:1) gave the title compound (111MF01) (4.09 g, 76%). 1H NMR (CDCl3) δ 6.93-6.87 (m, 1H), 6.92-6.88 (m, 1H), 6.68-6.63 (m, 1H), 4.56 (m, 2H), 4.01 (m, 1H), 3.78 (m, 1H), 3.58 (m, 1H), 3.45 (m, 1H), 2.11 (m, 1H), 0.92 (s, 12H), 0.06 (d, J=0.8 Hz, 6H); 13C NMR (CDCl3) δ 164.8, 158.5 (d, J=239.9 Hz), 141.6 (d, J=2.7 Hz), 130.1 (d, J=10.7 Hz), 117.6 (d, J=9.3 Hz), 109.6 (d, J=23.1 Hz), 103.6 (d, J=28.8 Hz), 67.8, 65.9, 44.2, 34.5, 26.0, 18.4, 14.9, −5.4, −5.4.
Source ID: ord-3152693a05684ad99a16f9451b1139c9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-Fluoro-4H-benzo[1,4]oxazin-3-one (8173MF55b) (0.090 g, 0.54 mmol), Cs2CO3 (0.263 g, 0.81 mmol) and 3-chloro-1-iodopropane (0.121 g, 0.59 mmol) were mixed according to GP5. CC (SiO2; Heptane/EtOAc 10:1-5) gave the title compound (8173MF55b) (0.102 g, 78%). 1HNMR(CDCl3) δ 6.95-6.91 (m, 1H), 6.82-6.78 (m, 1H), 6.72-6.67 (m, 1H), 4.57 (s, 1H), 4.05 (t, J=7.2 Hz, 2H), 3.62 (t, J=6.2 Hz, 2H), 2.19-2.11 (m, 2H); 13CNMR(CDCl3) δ 164.6, 158.6 (d, J=240.7 Hz), 141.5 (d, J=2.3 Hz), 129.6 (d, J=10.5 Hz), 118.0 (d, J=9.3 Hz), 110.0 (d, J=23.1 Hz), 102.7 (d, J=28.8 Hz), 67.8, 42.3, 39.3, 30.0.
Source ID: ord-9b2cbb0d58984737bfb1cc17c9500d6fPubChem References
These sources are listed in the compound's public database record.
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