Water → 4-(Trifluoromethyl)indoline

HRID 225572Notes

Reaction equation

HRID 225572 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 aqueous 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-1bc62934a31c4a219546eb3e7d81dd16
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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