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

HRID 557578Notes

Reaction equation

HRID 557578 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-96ce798c83d84b84ae4661e9d921f60b
Source dataset
uspto-grants-2011_11
Patent number
US08058441B2

Reaction notes

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