(3-Chlorophenyl)hydrazine → 4-chloro-3,3-dimethyl-2,3-dihydro-1H-indole

HRID 1475295Notes

Reaction equation

HRID 1475295 reaction equation
ClCC([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[C:7]([CH3:16])([CH3:15])[CH2:6]1)=O.[Cl:17][C:18]1[CH:19]=[C:20]([NH:24]N)[CH:21]=[CH:22][CH:23]=1>>[Cl:14][C:11]1[CH:12]=[C:13]2[C:8]([C:7]([CH3:16])([CH3:15])[CH2:6][NH:5]2)=[CH:9][CH:10]=1.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:19]=1[C:7]([CH3:15])([CH3:8])[CH2:6][NH:24]2

Participants

4

Reactant 2

HCID 75332(3-Chlorophenyl)hydrazineHCID 867239242-Chloro-1-(6-chloro-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone

Product 2

HCID 204468746-chloro-3,3-dimethyl-2,3-dihydro-1H-indoleYield 4%HCID 470025134-chloro-3,3-dimethyl-2,3-dihydro-1H-indoleYield 14%

Procedure

Step 1 of the synthesis of 2-chloro-1-(6-chloro-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone (Preparation 1) was repeated, using 3-chlorophenylhydrazine (1.0 g, 5.6 mmol) and the two isomers separated by chromatography on silica gel (gradient elution, 0-60% EtOAc/petrol then 0-100% Et2O/petrol), to give 6-chloro-3,3-dimethyl-2,3-dihydro-1H-indole (38 mg, 4%) as a yellow oil, 1H NMR (CDCl3): 6.93 (1H, d), 6.71 (1H, dd), 6.61 (1H, d), 3.34 (2H, s), 1.31 (6H, s) and 4-chloro-3,3-dimethyl-2,3-dihydro-1H-indole (146 mg, 14%), as a yellow oil, 1H NMR (Me-d3-OD): 6.93 (1H, t), 6.58 (1H, d), 6.53 (1H, d), 3.27 (2H, s), 1.43 (6H, s).

Workup

  1. customthe two isomers separated by chromatography on silica gel (
  2. washgradient elution, 0-60% EtOAc/petrol

Sources & evidence

ORD record
ord-a4af2b0d0dd04de8a145ccf1d462de92
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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