1,2-Dichloroethane → 1-(2-Chloroacetyl)indoline

HRID 1278905Notes

Reaction equation

HRID 1278905 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(Cl)(=[O:12])C.[Cl:14][CH2:15][CH2:16]Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:14][CH2:15][C:16]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)=[O:12]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 6367Acetyl chlorideHCID 10328Indoline

Product 1

HCID 1768971-(2-Chloroacetyl)indolineYield 85%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A quantity of 2,3-dihydro-1H-1-indole (also known as indoline, 2.1 g, 17.6 mmol) is dissolved in toluene (60 ml). To the solution of the amine in toluene is added acetyl chloride (2.0 g, 17.6 mmol) dissolved in 1,2-dichloroethane (20 ml). The reaction mixture turns brown upon addition of the acid chloride. The reaction is allowed to proceed at room temperature, with stirring, for about 3 hr, after which the reaction mixture is diluted with ethyl acetate and washed with 50:50 (v/v) water:saturated NaCl solution (2 times). The organic phase is dried over anhydrous MgSO4 and concentrate to yield 2-Chloro-1-(2,3-dihydro-1H-1-indolyl)-1-ethanone (may also be named 2-chloro-1-indolinylethan-1-one) in 85% yield (2.92 g, 15 mmol) as a light brown solid.

Workup

  1. customto proceed at room temperature
  2. washwashed with 50:50 (v/v) water
  3. dry with materialThe organic phase is dried over anhydrous MgSO4
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-c775d4c9a7a64e3c8a713e2bd65c2934
Source dataset
uspto-grants-2002_09
Patent number
US06444819B1

Reaction notes

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