6-hydroxy-7-nitro-2H-1,4-benzoxazin-3-(4H)-one → 7-Amino-6-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 280824Notes

Reaction equation

HRID 280824 reaction equation
[OH:1][C:2]1[C:3]([N+:13]([O-])=O)=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.[H][H]>CN(C=O)C.[Ni]>[OH:1][C:2]1[C:3]([NH2:13])=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1

Participants

5

Reactant 2

HCID 212986856-hydroxy-7-nitro-2H-1,4-benzoxazin-3-(4H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 212986837-Amino-6-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

The 6-hydroxy-7-nitro-2H-1,4-benzoxazin-3-(4H)-one (17.5 g) in DMF (300 ml) was reduced under 60 Atm. hydrogen at 60° C. in the presence of Ni Raney catalyst in an autoclave. The resulting amine was not isolated.

Workup

  1. customat 60° C.

Sources & evidence

ORD record
ord-d8b6b91826884765ad0f3cc0e1bd9034
Source dataset
uspto-grants-1986_05
Patent number
US04591548

Reaction notes

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