1-(2,2-Dimethyl-6-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethan-1-one → 1-(6-Amino-2,2-dimethyl-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethan-1-one

HRID 1197771Notes

Reaction equation

HRID 1197771 reaction equation
[C:1]([N:4]1[C:9]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:8]=2[O:7][C:6]([CH3:18])([CH3:17])[CH2:5]1)(=[O:3])[CH3:2]>C(O)C.[Ni]>[C:1]([N:4]1[C:9]2[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:8]=2[O:7][C:6]([CH3:18])([CH3:17])[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 219595781-(2,2-Dimethyl-6-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethan-1-one

Product 1

HCID 219594121-(6-Amino-2,2-dimethyl-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethan-1-oneYield 98.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 20.9 g 4-acetyl-3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazine in 200 ml ethanol, was added a catalytic amount of Raney nickel, and the catalytic hydrogenation was carried out at ordinary temperature and pressure. The catalyst was filtered off from the reaction mixture, and the solvent was distilled off from the filtrate, giving 18.2 g of crude 4-acetyl-6-amino-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine.

Workup

  1. filtrationThe catalyst was filtered off from the reaction mixture
  2. distillationthe solvent was distilled off from the filtrate

Sources & evidence

ORD record
ord-97449dc636c74e729e29114828197cea
Source dataset
uspto-grants-1994_01
Patent number
US05278158

Reaction notes

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