Acetic Anhydride → 1-Acetyl-1,2-dihydro-2,2,4-trimethylquinoline-6-carboxylic acid methyl ester

HRID 557570Notes

Reaction equation

HRID 557570 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([CH3:16])([CH3:15])[CH:9]=[C:8]2[CH3:17])=[O:4].[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:18](=[O:20])[CH3:19])[C:10]([CH3:16])([CH3:15])[CH:9]=[C:8]2[CH3:17])=[O:4]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 534161101,2-Dihydro-2,2,4-trimethylquinoline-6-carboxylic acid methyl ester

Product 1

HCID 669924781-Acetyl-1,2-dihydro-2,2,4-trimethylquinoline-6-carboxylic acid methyl ester

Procedure

A mixture of 1,2-dihydro-2,2,4-trimethylquinoline-6-carboxylic acid methyl ester (2.3 g) and a catalytic amount of N,N-dimethylaminopyridine in acetic anhydride (60 ml) was stirred at 100° C. for 18 h. The reaction mixture was concentrated in vacuo, the residue was dissolved in ethyl acetate and washed with water and brine. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silicagel in heptane/ethyl acetate=1/11/9 (v/v) as eluent.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silicagel in heptane/ethyl acetate=1/11/9 (v/v) as eluent

Sources & evidence

ORD record
ord-df7704be257c4bdc8e7ffbbf4b004075
Source dataset
uspto-grants-2011_11
Patent number
US08058441B2

Reaction notes

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