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

HRID 2382290Notes

Reaction equation

HRID 2382290 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=1/1=>1/9 (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=1/1=>1/9 (v/v) as eluent

Sources & evidence

ORD record
ord-65e4b1b047b8479d8036fac4049a6b71
Source dataset
uspto-grants-2012_09
Patent number
US08258293B2

Reaction notes

Loading…