Isatin → HCID 21906981, compound

HRID 2300276Notes

Reaction equation

HRID 2300276 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:10])[C:8]=1[OH:9])[NH2:5].N1C2C(=CC=CC=2)[C:14](=[O:15])[C:12]1=[O:13].Cl.[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][NH2:31])=[CH:26][CH:25]=1>>[OH:9][C:8]1[C:2]([CH3:1])=[C:3]2[C:4](=[CH:6][C:7]=1[CH3:10])[NH:5][C:12](=[O:13])[C:14]2=[O:15].[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][N:31]=[C:14]2[C:6]3[C:4](=[CH:3][C:2]([CH3:1])=[C:8]([OH:9])[C:7]=3[CH3:10])[NH:5][C:12]2=[O:13])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7054IsatinHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 826684-Amino-2,6-dimethylphenol

Product 2

HCID 21906981HCID 21906981, compoundHCID 178426640HCID 178426640, compound

Procedure

5-Hydroxy-4,6-dimethyl-1H-indole-2,3-dione was prepared from 3,5-dimethyl-4-hydroxyaniline according to Procedure A: 1H NMR (DMSO-d6): δ 2.17 (s, 3H), 2.30 (s, 3H), 6.45 (s, 1H), 8.29 (s, 1H), 10.65 (s, 1H); ESI-MS m/z 190 (M−H)−. The isatin was combined with 4-methylphenylhydrazine hydrochloride according to Procedure H to provide the title compound in 41% yield. 1H NMR (DMSO-d6): δ 2.15 (s, 3H), 2.24 (s, 3H), 2.43 (s, 3H), 6.46 (s, 1H), 7.16 (m, 4H), 7.88 (s, 1H), 10.64 (s, 1H 12.85 (s, 1H). APCI-MS m/z 294 (M−H, 45%).

Sources & evidence

ORD record
ord-5cc09d5298da469196219644f499caa1
Source dataset
uspto-grants-2002_12
Patent number
US06498176B1

Reaction notes

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