Acetyl chloride → Methyl 5-acetyl-2,3-dihydro-1H-indole-1-carboxylate

HRID 2307414Notes

Reaction equation

HRID 2307414 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)=[O:8].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[CH3:5][O:6][C:7]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:1](=[O:3])[CH3:2])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)=[O:8]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 690083Methyl 2,3-dihydro-1H-indole-1-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20744325Methyl 5-acetyl-2,3-dihydro-1H-indole-1-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Acetyl chloride (10.66 mL, 0.15 mol) was added slowly to a mixture of 2,3-dihydro-indole-1-carboxylic acid methyl ester, Preparation 17 (17 g, 0.1 mol), and aluminum chloride (40 g, 0.3 mol) in carbon disulfide (150 mL) at 0° C. The reaction mixture was warmed to room temperature and heated under reflux for 16 hours. The reaction mixture was then cooled to room temperature and poured into ice water. The resulting mixture was extracted with CH2Cl2 (3×40 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and the resultant filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica using ethyl acetate/hexane (30%) to provide the title product (8.8 g, 40%) as a solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. extractionThe resulting mixture was extracted with CH2Cl2 (3×40 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe resultant filtrate was concentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-35fc750602df4a49a7f0af27b35752c6
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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