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

HRID 1684570
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HRID 1684570 반응식
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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fbcc5e3df8d6401fb0e024afd5a354a4
출처 데이터셋
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05641788

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