3,4,5-Trimethoxyaniline → 5,6,7-Trimethoxy-2-methylquinoline

HRID 987425Notes

Reaction equation

HRID 987425 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].[CH:14](=O)/[CH:15]=[CH:16]/[CH3:17]>Cl>[CH3:17][C:16]1[CH:15]=[CH:14][C:7]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:9]([O:10][CH3:11])[C:8]=2[O:12][CH3:13])[N:6]=1

Participants

4

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 447466Crotonaldehyde

Product 1

HCID 140009745,6,7-Trimethoxy-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A 6 M hydrochloric acid solution (20 mL) of 3,4,5-trimethoxyaniline (3.1 g) was heated to 100° C., to which crotonaldehyde (1.5 mL) was slowly added dropwise. The mixture was stirred for 3.5 hours as it is. After allowing the reaction mixture to cool, it was washed with ether, and the resultant water layer was alkalified with a potassium carbonate solution. After extracted with ethyl acetate, the resultant organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the residue was then purified by column chromatography on silica gel (ethyl acetate:hexane=1:2 to 1:1) to obtain the title compound.

Workup

  1. additionwas slowly added dropwise
  2. temperatureto cool
  3. washit was washed with ether
  4. extractionAfter extracted with ethyl acetate
  5. washthe resultant organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customthe residue was then purified by column chromatography on silica gel (ethyl acetate:hexane=1:2 to 1:1)

Sources & evidence

ORD record
ord-6f0320a23009470b80388c19827a4ec2
Source dataset
uspto-grants-2003_10
Patent number
US06632810B2

Reaction notes

Loading…