Acetic Anhydride → 1-Acetyl-1,2,3,4-tetrahydroquinoline

HRID 1808334Notes

Reaction equation

HRID 1808334 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1>ClCCl>[N:8]1([C:5](=[O:7])[CH3:6])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 3478501-Acetyl-1,2,3,4-tetrahydroquinolineYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (55.5 g; 1.05 equiv.) was slowly added dropwise, at 0° C., to a solution of 1,2,3,4-tetrahydroquinoline (69 g; 1 equiv.) in 690 ml of dichloromethane. The reaction mixture was stirred for 30 minutes at room temperature and, when the conversion was complete, was washed with cold water and sodium hydrogen carbonate solution. The organic phase was dried over sodium sulfate and concentrated under reduced pressure. 1-(3,4-Dihydroquinolin-1(2H)-yl)ethanone (85 g; 94.4%) was obtained in the form of a colorless oil.

Workup

  1. washwas washed with cold water and sodium hydrogen carbonate solution
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-306dd9c923254a0b856838a4349f9191
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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