Acetyl chloride → HCID 11043471, compound

HRID 1108680Notes

Reaction equation

HRID 1108680 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH2:9]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([C:21]([O:23][CH3:24])=[O:22])[CH:15]=2)[CH2:10][CH3:11]>ClCCl>[C:5]([C:20]1[C:19]2[C:14](=[CH:15][C:16]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:18]=2)[NH:13][C:12]=1[CH2:9][CH2:10][CH3:11])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 22627295Methyl 2-propylindole-6-carboxylate

Product 1

HCID 11043471HCID 11043471, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a stirring suspension of aluminum chloride (294 mg) and acetyl chloride (0.08 ml) in dichloromethane (10 ml) was added methyl 2-propylindole-6-carboxylate (200 mg), and the mixture was stirred at 20° C. for 1 hour. The resulting mixture was poured onto ice and extracted with ethyl acetate. The combined organic phase was washed with aqueous sodium bicarbonate and brine, then dried over sodium sulfate and evaporated in vacuo. The residue was triturated with isopropyl ether to give methyl 3-acetyl-2-propylindole-6-carboxylate (78 mg) as colorless crystals.

Workup

  1. additionThe resulting mixture was poured onto ice
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated with isopropyl ether

Sources & evidence

ORD record
ord-a2818d9a0ca94456b7df75196a1e0f25
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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