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Sulfuric Acid → 3-Acetyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline

HRID 1684570
Notes
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Reaction equation

HRID 1684570 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[CH:21][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=O.[C:29]([CH2:32][C:33](=O)[CH3:34])(=[O:31])[CH3:30]>C(O)(=O)C>[C:29]([C:32]1[C:33]([CH3:34])=[N:6][C:7]2[C:8]([C:9]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=[CH:21][C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=2)(=[O:31])[CH3:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 31261AcetylacetoneHCID 99269672-Amino-4,5,3',4'-tetramethoxybenzophenone

Product 1

HCID 190398893-Acetyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinolineYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Conc. sulfuric acid (0.185 ml ) was added to a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (10.0 g), acetylacetone (3.78 g) and acetic acid (75 ml), and the mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was poured into water and made alkaline with 2N sodium hydroxide, and extracted with chloroform. The chloroform layer was washed with water and 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-ethanol (20:1, v/v) gave 3-acetyl-4-(3,4-dimethoxyphenyl )-6,7-dimethoxy-2-methyl-quinoline (9.78 g, 82%). This compound was recrystallized from dichloromethane-ethanol to give colorless prisms, mp. 210°-211° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was poured into water
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washThe fractions eluted with chloroform-ethanol (20:1

Sources & evidence

ORD record
ord-fbcc5e3df8d6401fb0e024afd5a354a4
Source dataset
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05641788

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes