Acetyl chloride → 1-(2,3-Dihydro-1H-indol-1-yl)ethan-1-one

HRID 73958

Reaction equation

HRID 73958 reaction equation
C([O-])(O)=O.[Na+].[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1.[C:15](Cl)(=[O:17])[CH3:16]>C(Cl)Cl>[N:6]1([C:15](=[O:17])[CH3:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10328IndolineHCID 516892Sodium Bicarbonate

Product 1

HCID 276731-(2,3-Dihydro-1H-indol-1-yl)ethan-1-oneYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of NaHCO3 (504 g, 6.0 mol) and 2,3-dihydro-1H-indole (60 g, 0.5 mol) in CH2Cl2 (600 mL) cooled in an ice-water bath, was added dropwise acetyl chloride (78.5 g, 1.0 mol). The mixture was stirred at room temperature for 2 h. The solid was filtered off and the filtrate was concentrated to give 1-(2,3-dihydro-indol-1-yl)-ethanone (82 g, 100%).

Workup

  1. temperaturecooled in an ice-water bath
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0295631caa6f40c8a2682d5ec788b471
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Linked notes

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