Chloroacetyl chloride → 2-Chloro-1-(3-phenyl-2,3-dihydro-1H-indol-1-yl)ethan-1-one

HRID 262292Notes

Reaction equation

HRID 262292 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:16][CH2:17][C:18](Cl)=[O:19].C([O-])(=O)C.[Na+]>CC(C)=O.O>[Cl:16][CH2:17][C:18]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8]1)=[O:19]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 517045Sodium AcetateHCID 109323533-phenyl-2,3-dihydro-1H-indole

Product 1

HCID 213204582-Chloro-1-(3-phenyl-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 11.1 g of 3-phenylindoline in 60 ml of acetone was cooled to 0° C., 5.1 ml of chloroacetylchloride was added and the mixture poured into an ice cold solution of 10 g of sodium acetate in 50 ml of water. The mixture was then stirred for one hour at room temperature and the residual solid removed by filtration. Recrystallization from ethanol gave a yield of 13.0 g of the desired N-chloroacetyl-3-phenylindoline having a melting point of 76°-78° C.

Workup

  1. customthe residual solid removed by filtration
  2. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-bcbdb4dd53a6427982ebe462654130e2
Source dataset
uspto-grants-1979_05
Patent number
US04153789

Reaction notes

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