Acetic Anhydride → 1-(4,4-dimethyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

HRID 22817Notes

Reaction equation

HRID 22817 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH3:8][C:9]1([CH3:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][NH:11][CH2:10]1>ClCCl>[CH3:8][C:9]1([CH3:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][N:11]([C:5](=[O:7])[CH3:6])[CH2:10]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1921721,2,3,4-Tetrahydro-4,4-dimethylisoquinoline

Product 1

HCID 225920161-(4,4-dimethyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanoneYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of acetic anhydride (1.17 ml, 12.4 mmol) was added dropwise to a stirred, ice-cooled solution of 4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline (1.0 g, 6.2 mmol) (for preparation see J. Org. Chem., 1983, 48, 5348) in dry dichloromethane (5 ml). The cooling bath was removed and the solution was stirred for 2 h at room temperature. The reaction mixture was then concentrated in vacuo to give the title compound (D2) as an oil (1.1 g, 87%), δH (CDCl3, rotamers observed)/ppm 1.28, 1.32 (6H, 2×s), 2.20, 2.22 (3H, 2×s), 3.43, 3.61 (2H, 2×s), 4.66, 4.77 (2H, 2×s), 7.07-7.37 (4H, m).

Workup

  1. customThe cooling bath was removed
  2. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-2fda999bbb6a4c1d92fac45c4d7ae8b4
Source dataset
uspto-grants-2005_02
Patent number
US06849644B2

Reaction notes

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