Acetic Anhydride → HCID 67392217, compound

HRID 907390Notes

Reaction equation

HRID 907390 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=2)[N:3]=1.[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1.C(OC(=O)C)(=O)C>[Cl-].[Zn+2].[Cl-]>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20](/[CH:21]=[CH:1]/[C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=3)[N:3]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 312444-MethoxybenzaldehydeHCID 6044832-Methylquinoline-6-carboxylic acid

Product 1

HCID 67392217HCID 67392217, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A mixture of 2-methyl-6-quinolinecarboxylic acid (200 mg, 0.936 mmol), 4-methoxybenzaldehyde (228 mg, 0.936 mmol), acetic anhydride (630 mg, 6.18 mmol) and a catalytic amount of zinc chloride was heated at 140° C. for 12 h with stirring. The cooled reaction mixture was extracted with water and ethyl acetate. The organic layer was collected, dried (MgSO4) and the solvent was removed under reduced pressure to give dark brown solid. This material was applied to a silica gel column and the product was eluted with ethyl acetate/n-hexane (1/4). Fractions containing the required product (RF=0.20 ethyl acetate/n-hexane 2/1, fluorescent under UV lamp) were collected and the solvents were removed under reduced pressure. The residue as a yellow solid was triturated with n-hexane and filtered to give the title compound (71 mg, 25%), m.p.=274-277° C. (sublimed around 240° C.).

Workup

  1. customThe cooled reaction mixture
  2. extractionwas extracted with water and ethyl acetate
  3. customThe organic layer was collected
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed under reduced pressure
  6. customto give dark brown solid
  7. washthe product was eluted with ethyl acetate/n-hexane (1/4)
  8. additionFractions containing the required product (RF=0.20 ethyl acetate/n-hexane 2/1, fluorescent under UV lamp)
  9. customwere collected
  10. customthe solvents were removed under reduced pressure
  11. customThe residue as a yellow solid was triturated with n-hexane
  12. filtrationfiltered

Sources & evidence

ORD record
ord-97f020260deb4879b9827e8d3b731e48
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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