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

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Reaction Steps

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.

Provenance & Evidence