Water → 5-Nitro-3,4-dihydro-2H-1,4-benzoxazine
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].Br[CH2:13][CH2:14]Br.[OH-].[K+].O>CN(C)C=O>[N+:8]([C:7]1[C:2]2[NH:1][CH2:14][CH2:13][O:11][C:3]=2[CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
To a solution of 2-amino-3-nitrophenol (15.0 g, 97 mmol) and 1,2-dibromoethane (29.1 g, 155 mmol) in dimethylformamide (80 mL) was added KOH (10.9 g, 194 mmol) at 180° C. After stirring at 200° C. for 2 days, the mixture was poured to 150 g water. The mixture was concentrated under reduced pressure. The crude product was purified using column chromatography to give the title compound (2.50 g) as a red solid. MS (ESI): m/z 181 [M+H]+
Workup
- concentrationThe mixture was concentrated under reduced pressure
- customThe crude product was purified
Sources & evidence
- ORD record
- ord-54d706f37cf44ef6bb24c7d791c52aa0
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969349B2
Reaction notes
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