Benzoylacetone → HCID 19039879, compound

HRID 1684572Notes

Reaction equation

HRID 1684572 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.[C:25]([CH2:33][C:34](=O)[CH3:35])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C>[C:25]([C:33]1[C:34]([CH3:35])=[N:2][C:3]2[C:4]([C:5]=1[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)=[CH:17][C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 7166BenzoylacetoneHCID 214661342-Amino-3',4',4,5-tetramethoxybenzophenone hydrochloride

Product 1

HCID 19039879HCID 19039879, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4,5,3',4'-tetramethoxy-benzophenone hydrochloride (2.0 g), benzoylacetone (0.917 g) and ethanol (35 ml) was stirred under reflux for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was poured into a saturated aqueous solution of sodium bicarbonate, and the mixture was extracted with chloroform. The chloroform layer was washed with water, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (10:1, v/v) gave 3-benzoyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline (1.75 g, 70%). This compound was recrystallized from ethanol to give colorless prisms, mp. 151°-152° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was poured into a saturated aqueous solution of sodium bicarbonate
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. washThe fractions eluted with chloroform-ethyl acetate (10:1

Sources & evidence

ORD record
ord-03f9dcf9fe014bb4a1bd18ba671202ca
Source dataset
uspto-grants-1997_06
Patent number
US05641788

Reaction notes

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