Methanol → 4-acetyl 6-amino-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1,4-benzoxazine

HRID 1197773Notes

Reaction equation

HRID 1197773 reaction equation
[C:1]([N:4]1[C:9]2[CH:10]=[C:11]([NH:17]C(=O)C(F)(F)F)[C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=2[O:7][C:6]([CH3:25])([CH3:24])[CH2:5]1)(=[O:3])[CH3:2].CO.C(=O)(O)[O-].[Na+]>O>[C:1]([N:4]1[C:9]2[CH:10]=[C:11]([NH2:17])[C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=2[O:7][C:6]([CH3:25])([CH3:24])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 191048224-acetyl-3,4-dihydro-2,2-dimethyl-7-nitro-6-trifluoroacetylamino-2H-1,4-benzoxazine

Product 1

HCID 191048204-acetyl 6-amino-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1,4-benzoxazineYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21.6 g 4-acetyl-3,4-dihydro-2,2-dimethyl-7-nitro-6-trifluoroacetylamino-2H-1,4-benzoxazine, 500 ml methanol, 50 ml water and 10.5 g sodium bicarbonate was stirred at room temperature for seven hours, the reaction mixture was poured into 1.5 l ice water, and the precipitate which separated out was collected by filtration and recrystallized from 450 ml ethanol, giving 13.5 g of 4-acetyl-6-amino-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1,4-benzoxazine.

Workup

  1. customthe precipitate which separated out
  2. filtrationwas collected by filtration
  3. customrecrystallized from 450 ml ethanol

Sources & evidence

ORD record
ord-d9c1f5b2f1754a0d8280fa239f3dada8
Source dataset
uspto-grants-1994_01
Patent number
US05278158

Reaction notes

Loading…