Nitric Acid → 4-acetyl-3,4-dihydro-2,2-dimethyl-7-nitro-6-trifluoroacetylamino-2H-1,4-benzoxazine

HRID 1197772Notes

Reaction equation

HRID 1197772 reaction equation
[C:1]([N:4]1[C:9]2[CH:10]=[C:11]([NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:13][C:8]=2[O:7][C:6]([CH3:22])([CH3:21])[CH2:5]1)(=[O:3])[CH3:2].[N+:23]([O-])([OH:25])=[O:24]>C(O)(=O)C>[C:1]([N:4]1[C:9]2[CH:10]=[C:11]([NH:14][C:15](=[O:20])[C:16]([F:18])([F:19])[F:17])[C:12]([N+:23]([O-:25])=[O:24])=[CH:13][C:8]=2[O:7][C:6]([CH3:22])([CH3:21])[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 191048184-acetyl-3,4-dihydro-2,2-dimethyl-6-trifluoroacetylamino-2H-1,4-benzoxazine

Product 1

HCID 191048224-acetyl-3,4-dihydro-2,2-dimethyl-7-nitro-6-trifluoroacetylamino-2H-1,4-benzoxazine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 22.0 g 4-acetyl-3,4-dihydro-2,2-dimethyl-6-trifluoroacetylamino-2H-1,4-benzoxazine in 100 ml acetic acid, was added dropwise a solution of 3.7 ml fuming nitric acid in 50 ml acetic acid, and the resulting solution was stirred at room temperature for two hours. The reaction mixture was poured into 600 ml ice water, the crystals which separated out were collected by filtration, and recrystallized from 100 ml ethanol, giving 21.6 g of 4-acetyl-3,4-dihydro-2,2-dimethyl-7-nitro-6-trifluoroacetylamino-2H-1,4-benzoxazine.

Workup

  1. customthe crystals which separated out
  2. filtrationwere collected by filtration
  3. customrecrystallized from 100 ml ethanol

Sources & evidence

ORD record
ord-6525a8214b3e4536b0078c707bfd67ee
Source dataset
uspto-grants-1994_01
Patent number
US05278158

Reaction notes

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