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

HRID 720317Notes

Reaction equation

HRID 720317 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-b300e19a1a534c2ab471cb29b1672e9e
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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