Hydroxylamine → Indole-2,3-dione, 5,6-dimethyl-

HRID 2414093Notes

Reaction equation

HRID 2414093 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].Cl[C:11](Cl)(Cl)[CH:12]([OH:14])O.N[OH:18].S(=O)(=O)(O)[OH:20]>>[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:4]2[C:3]=1[C:12](=[O:14])[C:11](=[O:20])[NH:5]2.[CH3:9][C:8]1[CH:7]=[C:6]2[C:4](=[CH:3][C:2]=1[CH3:1])[NH:5][C:11](=[O:18])[C:12]2=[O:14]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 1118Sulfuric AcidHCID 2707Chloral HydrateHCID 72483,4-Dimethylaniline

Product 2

HCID 52550Indole-2,3-dione, 5,6-dimethyl-HCID 2665354,5-Dimethylisatin

Procedure

3,4-Dimethylaniline was converted into 3,4-dimethyl-isonitrosoacetanilide by reaction with chloral hydrate and hydroxylamine, using the method described in "Organic Syntheses," Collective Volume I, page 327. The 3,4-dimethyl-isonitrosoacetanilide was cyclized with sulfuric acid, according to the method of Baker et al., Journal of Organic Chemistry, 17, 149 (1952), to give 4,5-dimethylisatin (m.p. 225°-226° C.) and 5,6-dimethylisatin (m.p. 217°-218° C.).

Sources & evidence

ORD record
ord-63aa5800f95f45ddae420474d4e00a14
Source dataset
uspto-grants-1988_01
Patent number
US04721712

Reaction notes

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