Acetyl chloride → N-Acetyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline

HRID 1382913Notes

Reaction equation

HRID 1382913 reaction equation
[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.[C:13](Cl)(=[O:15])[CH3:14]>>[C:13]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([CH3:12])([CH3:1])[CH2:3][CH2:4]1)(=[O:15])[CH3:14]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 132194414,4-Dimethyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 14372186N-Acetyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolineYield 99%

Procedure

To a stirred solution of 15 g (0.93 mol) of 4,4-dimethyl-1,2,3,4-tetrahydroquinoline in 50 ml of pryidine, at 0° C., was added, dropwise, 14.5 g (0.185 mol) of acetyl chloride over a 30 minute period. Stirring was continued at 0° C. for 1 hour, and then the reaction mixture was poured onto 200 g of ice. The resulting mixture was extracted with ether. The combined organic extracts were washed successively with 1N hydrochloric acid and saturated sodium bicarbonate and then they were dried using magnesium sulfate. Evaporation of the ether solution in vacuo afforded 18.8 g (99% yield) of the title compound as a yellow oil.

Workup

  1. extractionThe resulting mixture was extracted with ether
  2. washThe combined organic extracts were washed successively with 1N hydrochloric acid and saturated sodium bicarbonate
  3. customthey were dried
  4. customEvaporation of the ether solution in vacuo

Sources & evidence

ORD record
ord-31990bd77f204f76912a9d8393bce6ab
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

Loading…