Chloroacetyl chloride → 5-(2-chloroacetyl)-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

HRID 1087044Notes

Reaction equation

HRID 1087044 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:17][CH2:18][C:19](Cl)=[O:20]>ClCCl>[Cl:17][CH2:18][C:19]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3](=[O:11])[C:2]2([CH3:12])[CH3:1])=[O:20]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 107523795-(2-chloroacetyl)-3,3-dimethyl-2,3-dihydro-1H-indol-2-oneYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.8 g (66.4 mmoles) 3,3-dimethyl-3H-indol-2-one are slowly added (in 1 h) to a suspension of 26 7 g (200 mmoles) aluminium chloride and 15 g, that is 10.58 ml (133 mmoles) chloroacetyl chloride in 60 ml dichloromethane, then the mixture is heated under reflux for 1 h 30 min. The brown suspension obtained is slowly poured into 500 ml ice-water, the mixture is stirred for 30 min and then filtered and the solid is washed with a little ether and dried. 16.3 g of crystals are obtained, which are used as such in the following step.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 1 h 30 min
  3. customThe brown suspension obtained
  4. filtrationfiltered
  5. washthe solid is washed with a little ether
  6. customdried

Sources & evidence

ORD record
ord-32872acd133a4693bd4560d2c204ec1f
Source dataset
uspto-grants-1991_07
Patent number
US05034401

Reaction notes

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