Triethylamine → 3-Bromo-1-(3-phenyl-2,3-dihydro-1H-indol-1-yl)propan-1-one
Reaction equation
[Br:1][CH2:2][CH2:3][C:4](Cl)=[O:5].[C:7]1([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C1C=CC=CC=1>[Br:1][CH2:2][CH2:3][C:4]([N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:14]1)=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
A solution of 9.1 ml of 3-bromopropionylchloride in 10 ml of dry benzene was added dropwise to a solution of 10.0 g of 3-phenylindoline and 10 ml of triethylamine in 100 ml of dry benzene cooled to 10° C. The precipitated triethylamine hydrochloride was separated by filtration, the benzene was removed from the filtrate in vacuo at room temperature and the residue recrystallized from ethanol to give 5.6 g of the desired N-(3-bromopropionyl)-3-phenylindoline having a melting point of 98°-9° C.
Workup
- customThe precipitated triethylamine hydrochloride was separated by filtration
- customthe benzene was removed from the filtrate in vacuo at room temperature
- customthe residue recrystallized from ethanol
Sources & evidence
- ORD record
- ord-f8eb417eb50d445cbd2f5e7abb475f60
- Source dataset
- uspto-grants-1979_05
- Patent number
- US04153789
Reaction notes
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