Water → 5-phenyl-2,3-dihydro-1H-indole

HRID 356021Notes

Reaction equation

HRID 356021 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].O.[OH-].[Na+]>C(O)(=O)C>[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH2:11][CH2:10]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 114582105-phenyl-1H-indole

Product 1

HCID 134974755-phenyl-2,3-dihydro-1H-indoleYield 93.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Phenylindole (D29) (0.85 g, 4.4 mmoles) was dissolved in glacial acetic acid (20 ml) and treated with sodium cyanoborohydride (1.34 g, 22 mmoles) at ambient temperature for 2 hrs. Water (100 ml) was added and the mixture basified with sodium hydroxide. Extraction with dichloromethane gave the title compound (D30) (0.8 g, 93%).

Workup

  1. extractionExtraction with dichloromethane

Sources & evidence

ORD record
ord-30430f06a5fc48ba9d15099162d111a8
Source dataset
uspto-grants-1998_11
Patent number
US05834494

Reaction notes

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