2,4-Octanedione → 4-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-2-methyl-3-valerylquinoline

HRID 1684575Notes

Reaction equation

HRID 1684575 reaction equation
Cl.[NH2:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)=O.[CH3:25][C:26](=O)[CH2:27][C:28](=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32]>C(O)C>[CH3:16][O:15][C:9]1[CH:8]=[C:7]([C:5]2[C:4]3[C:3](=[CH:20][C:19]([O:21][CH3:22])=[C:18]([O:23][CH3:24])[CH:17]=3)[N:2]=[C:26]([CH3:25])[C:27]=2[C:28](=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32])[CH:12]=[CH:11][C:10]=1[O:13][CH3:14]

Participants

4

Reactant 2

HCID 841922,4-OctanedioneHCID 214661342-Amino-3',4',4,5-tetramethoxybenzophenone hydrochloride

Product 1

HCID 190398844-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-2-methyl-3-valerylquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-3',4',4,5-tetramethoxybenzophenone hydrochloride (25.0 g), 2,4-octanedione (10.5 g) and ethanol (500 ml) was stirred under reflux for 2 hours. The solvent was evaporated under reduced pressure. The residue was poured into saturated aqueous sodium bicarbonate solution, and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate. The chloroform was evaporated, and the residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethanol (20:1, v/v) gave 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-3-valerylquinoline- This compound was recrystallized from ethanol to give colorless prisms. mp. 119°-120° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionThe residue was poured into saturated aqueous sodium bicarbonate solution
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe chloroform was evaporated
  8. washThe fractions eluted with chloroform-ethanol (20:1

Sources & evidence

ORD record
ord-36d856bfbf87411dbac9f995e8dda395
Source dataset
uspto-grants-1997_06
Patent number
US05641788

Reaction notes

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