Acetyl chloride → 1-(6-Methoxy-2,2,4-trimethylquinolin-1(2H)-yl)ethan-1-one

HRID 2382297Notes

Reaction equation

HRID 2382297 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH3:18])([CH3:17])[CH:11]=[C:10]2[CH3:19]>N1C=CC=CC=1>[C:1]([N:13]1[C:14]2[C:9](=[CH:8][C:7]([O:6][CH3:5])=[CH:16][CH:15]=2)[C:10]([CH3:19])=[CH:11][C:12]1([CH3:18])[CH3:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 421426HCID 421426, compound

Product 1

HCID 133701081-(6-Methoxy-2,2,4-trimethylquinolin-1(2H)-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride (8 ml) was added dropwise to a cooled (0° C.) solution of 1,2-dihydro-6-methoxy-2,2,4-trimethylquinoline (1.7 g) and a catalytic amount of N,N-dimethylaminopyridine in pyridine (60 ml). After stirring for 18 h, the reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane and washed with 1 M HCl, water, 5% aq. NaHCO3, water and brine. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silicagel in dichloromethane as eluent.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with 1 M HCl, water, 5% aq. NaHCO3, water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silicagel in dichloromethane as eluent

Sources & evidence

ORD record
ord-47c72612624347fea88cc9938789c2f1
Source dataset
uspto-grants-2012_09
Patent number
US08258293B2

Reaction notes

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