Dimethylformamide → 5-Nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 2235811Notes

Reaction equation

HRID 2235811 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][C:14](OCC)=[O:15].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[N+:8]([C:7]1[C:2]2[NH:1][C:14](=[O:15])[CH2:13][O:11][C:3]=2[CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 107741655-Nitro-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-amino-3-nitrophenol (1.54 g, 10 mmol), ethyl bromoacetate (1.67 g, 10 mmol), potassium carbonate (1.54 g, 11 mmol) and DMF (5.0 mL) was stirred at room temperature for 20 h. Reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL×3). Combined ethyl acetate layers were washed with water (50 mL×2), dried (brine, sodium sulphate), concentrated and dried on high vacuum to give 5-Nitro-4H-benzo[1,4]oxazin-3-one, K-64 (1.6 g).

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate (100 mL×3)
  3. washCombined ethyl acetate layers were washed with water (50 mL×2)
  4. dry with materialdried (brine, sodium sulphate)
  5. concentrationconcentrated
  6. customdried on high vacuum

Sources & evidence

ORD record
ord-b4fca33ea2a6468594c6b58979435362
Source dataset
uspto-grants-2010_05
Patent number
US07714017B2

Reaction notes

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