4-Amino-2-chloro-6-methylphenol → HCID 21956290, compound

HRID 840894Notes

Reaction equation

HRID 840894 reaction equation
ClC1C=C(C=C(C)C=1O)N.[Cl:11][C:12]1[C:20]([OH:21])=[C:19]([CH3:22])[CH:18]=[C:17]2[C:13]=1[C:14](=[O:24])[C:15](=[O:23])[NH:16]2.[CH:25]1[C:30]([NH:31][NH2:32])=[CH:29][CH:28]=[C:27]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:26]=1.Cl>>[Cl:11][C:12]1[C:20]([OH:21])=[C:19]([CH3:22])[CH:18]=[C:17]2[C:13]=1[C:14](=[O:24])[C:15](=[O:23])[NH:16]2.[Cl:11][C:12]1[C:20]([OH:21])=[C:19]([CH3:22])[CH:18]=[C:17]2[C:13]=1[C:14](=[N:32][NH:31][C:30]1[CH:29]=[CH:28][C:27]([S:33]([NH2:36])(=[O:34])=[O:35])=[CH:26][CH:25]=1)[C:15](=[O:23])[NH:16]2

Participants

5

Reactant 3

HCID 27744394-Amino-2-chloro-6-methylphenolHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 21956290HCID 21956290, compound

Product 2

HCID 21956290HCID 21956290, compoundHCID 178422040HCID 178422040, compound

Procedure

4-Chloro-5-hydroxy-6-methyl-1H-indole-2,3-dione was prepared from 3-chloro-4-hydroxy-5-methyl aniline according to Procedure A and employing flash chromatography (hexanes:EtOAc 1:1) to isolate the desired isomer: 1H NMR (DMSO-d6): δ2.35 (s, 3H), 6.67 (s, 1H), 9.17 (s, 1H), 10.81 (s, 1H); APCI−MS: m/z 210 (M−H)−. Anal. Calcd for C9H6NO3Cl: C, 51.08; H, 2.85; N, 6.62; Cl, 16.75. Found: C, 51.20; H, 2.90; N, 6.67; Cl, 16.85. The title compound was prepared from 4-chloro-5-hydroxy-6-methyl-1H-indole-2,3-dione and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G in 95% yield: mp>250° C.; 1H NMR (DMSO-d6): δ2.26 (s, 3H), 6.69 (s, 1H), 7.28 (s, 1H), 7.57 (d, J=8.8 Hz, 2H), 7.82 (d, J=8.8 Hz, 2H), 8.84 (s,1H), 11.02 (s,1H), 13.00 (s, 1H); APCI−MS: m/z 379 (M−H)−. Anal. Calcd for C15H13N4O4ClS: C, 47.31; H, 3.44; N, 14.71; Cl, 9.31; S, 8.42. Found: C,47.20; H, 3.47; N, 14.64; Cl, 9.41; S, 8.32.

Workup

  1. customto isolate the desired isomer

Sources & evidence

ORD record
ord-85d390600df3495fa666e81e9dc6c257
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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