Water → 4-(Trifluoromethyl)indoline

HRID 1930848Notes

Reaction equation

HRID 1930848 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.C([BH3-])#N.[Na+].O.[OH-].[Na+]>C(O)(=O)C>[F:13][C:2]([F:1])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][NH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 198037034-(Trifluoromethyl)-1H-indole

Product 1

HCID 162444454-(Trifluoromethyl)indolineYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.4 mmol of 4-trifluoromethyl-1H-indole were dissolved in 8 ml acetic acid. 8.8 mmol of sodium cyanoborohydride were added at once and the reaction mixture stirred at room temperature for 3.5 hours. 20 ml of water were added. The reaction mixture is treated with acqueous sodium hydroxide 40% until basic. Extraction with ethyl acetate yields the crude title compound as a yellowish waxy solid. Yield=76%. MS (m/e): 188.4 ([M+H]+, 97%).

Workup

  1. extractionExtraction with ethyl acetate

Sources & evidence

ORD record
ord-262f2ab0a4f1441f8925bf33df896204
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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