Propanoic acid, 2-bromo-2-methyl-, ethyl ester → 2,2-Dimethyl-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one
Reaction equation
[F-].[K+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[OH:13].Br[C:15]([CH3:22])([CH3:21])[C:16](OCC)=[O:17]>CN(C)C=O>[CH3:21][C:15]1([CH3:22])[C:16](=[O:17])[NH:3][C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=2[O:13]1Participants
Procedure
To a suspension of potassium fluoride (4.71 g) in N,N-dimethylformamide (40 mL) was added 2-amino-5-nitrophenol (5.00 g), and the mixture was stirred at room temperature for 1 hour. To the suspension was added dropwise a solution of ethyl α-bromoisobutyrate (6.33 g) in N,N-dimethylformamide (10 mL) over a period of 20 minutes, and the mixture was stirred at 60° C. for 20 hours. After cooling, to the reaction mixture was added cool, water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with an aqueous 10% HCl solution, water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was suspended in ethyl acetate, and the precipitates were collected by filtration and washed with ethyl acetate to give 2,2-dimethyl-7-nitro-2H-1,4-benzoxazin-3(4H)-one (2.80 g) as a pale brown powder.
Workup
- stirringthe mixture was stirred at 60° C. for 20 hours
- temperatureAfter cooling, to the reaction mixture
- additionwas added
- temperaturecool
- extractionwater and the mixture was extracted with ethyl acetate
- washThe organic layer was washed successively with an aqueous 10% HCl solution, water and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- filtrationthe precipitates were collected by filtration
- washwashed with ethyl acetate
Sources & evidence
- ORD record
- ord-e15370907b984a2a9b3ede011a4f0051
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07998956B2
Reaction notes
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