Water → 4-(Trifluoromethyl)indoline
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]2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- 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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