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

HRID 34699Notes

Reaction equation

HRID 34699 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:14][CH2:13][C:12](=[O:15])[NH:11][C:10]=2[CH:16]=1>C(O)(=O)C>[OH:5][C:6]1[C:7]([N+:1]([O-:4])=[O:2])=[CH:8][C:9]2[O:14][CH2:13][C:12](=[O:15])[NH:11][C:10]=2[CH:16]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 113786896-Hydroxy-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 212986856-hydroxy-7-nitro-2H-1,4-benzoxazin-3-(4H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Fumic nitric acid (δ 1.52, 2.6 ml, 0.062 mole) in acetic acid (5 ml) was added dropwise under stirring to 6-hydroxy-2H-1,4-benzoxazin-3-(4H)-one (Coupler (1), 10.3 g, 0.062 mole) in acetic acid (100 ml) at room temperature. The 6-hydroxy-7-nitro-1,4-benzoxazin-3-one (6.7 g, 51%) separated as yellow prisms.

Workup

  1. customThe 6-hydroxy-7-nitro-1,4-benzoxazin-3-one (6.7 g, 51%) separated as yellow prisms

Sources & evidence

ORD record
ord-d29846ee8c384435adf5c7c1588d6c1e
Source dataset
uspto-grants-1988_08
Patent number
US04762925

Reaction notes

Loading…