Water → 6-Fluoro-7-(methylamino)-3-(4-nitrophenyl)-2,3-dihydrobenzo[e][1,3]oxazin-4-one

HRID 1271047Notes

Reaction equation

[F:1][C:2]1[C:3](F)=[CH:4][C:5]2[O:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[C:7](=[O:20])[C:6]=2[CH:21]=1.[CH3:23][NH2:24].O>CS(C)=O>[F:1][C:2]1[C:3]([NH:24][CH3:23])=[CH:4][C:5]2[O:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[C:7](=[O:20])[C:6]=2[CH:21]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To 6,7-difluoro-3-(4-nitrophenyl)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.05 g, 0.16 mmol) in dimethyl sulfoxide (0.5 ml) was added methyl amine (0.3 ml, 2M solution in tetrahydrofuran) and the reaction heated to 140° C. for 1 hr. Water was added and product extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated to give 0.42 mg (81%) of 6-fluoro-7-(methylamino)-3-(4-nitrophenyl)-2,3-dihydrobenzo[e][1,3]oxazin-4-one. RP-HPLC: 2.38 min; ES-MS (M+H)+=318.0; 1H-NMR (DMSO-d6) δ (ppm): 3.1 (s, 3 H), 5.73 (s, 2 H), 6.2 (d, 1 H), 7.38 (d, 1 H), 7.61 (d, 1 H), 8.2 (d, 2 H).

Workup

extractionproduct extracted with ethyl acetate
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-533b84271b0e401296c6eb8f2d62c42a
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07205296B2

Reaction notes

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