Sulfuric Acid → 9-Hydroxy-5-benzo[a]phenoxazone-8-carboxylic acid 12-oxide

HRID 1031772Notes

Reaction equation

HRID 1031772 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]=[O:13])=[C:4]([OH:14])[CH:3]=1.[OH:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21](O)[C:17]=1[C:18]([OH:20])=[O:19].S(=O)(=O)(O)O>>[OH:15][C:16]1[CH:24]=[CH:23][C:22]2[N+:12]([O-:13])=[C:5]3[C:4](=[CH:3][C:2](=[O:1])[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=43)[O:14][C:21]=2[C:17]=1[C:18]([OH:20])=[O:19]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 93382,6-Dihydroxybenzoic AcidHCID 264074(1Z)-2-Hydroxynaphthoquinone 1-oxime

Product 1

HCID 566343899-Hydroxy-5-benzo[a]phenoxazone-8-carboxylic acid 12-oxide

Procedure

2.84 g. 1,3-dihydroxy-4-nitrosonaphthalene, 2.31 g. 2,6-dihydroxybenzoic acid, 1.29 g, pyrolusite and 1.6 ml. concentrated sulphuric acid are reacted analogously to Example 1(a). Yield 2.8 g.

Sources & evidence

ORD record
ord-fb9a7b54fcd24343979624d0d171f2c0
Source dataset
uspto-grants-1990_09
Patent number
US04954630

Reaction notes

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