Methane → 6,7-dihydro-9-methoxy-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

HRID 597521

반응식

HRID 597521 반응식
C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8]CC)=[O:7])C.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH2:23][CH2:22][CH2:21]2.[OH-].[Na+].C>O>[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:25]3[N:24]([CH:4]=[C:5]([C:6]([OH:8])=[O:7])[C:11]2=[O:13])[CH2:23][CH2:22][CH2:21][C:20]=3[CH:19]=1

참가 물질

6

반응물 4

HCID 297MethaneHCID 6871Diethyl (ethoxymethylene)malonateHCID 14798Sodium HydroxideHCID 67113Quinoline, 1,2,3,4-tetrahydro-6-methoxy-

생성물 1

HCID 130943606,7-dihydro-9-methoxy-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
220 °C

실험 절차

Diethyl ethoxymethylenemalonate (43.2 g., 0.20 mole) and 6-methoxytetrahydroquinoline (32.6 g., 0.20 mole) are mixed and heated at 125°-130° C. for three hours. Polyphosphoric acid (200 g.) is added, and the mixture is heated gradually to 220° C. then maintained at 220° C. for one hour. The mixture containing the product ester of Formula III is poured into about 600 ml. of water, then made basic with 40 percent sodium hydroxide solution and heated on a steam bath for two hours. The solution is treated with decolorizing charcoal, filtered and acidified. The solid product is isolated by filtration, washed with water and ethanol, then recrystallized from N,N-dimethylformamide to give 6,7-dihydro-9-methoxy-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, m.p. 253°-257° C.

후처리

  1. temperatureheated at 125°-130° C. for three hours
  2. temperaturethen maintained at 220° C. for one hour
  3. additionis poured into about 600 ml
  4. temperatureheated on a steam bath for two hours
  5. filtrationfiltered
  6. customThe solid product is isolated by filtration
  7. washwashed with water and ethanol
  8. customrecrystallized from N,N-dimethylformamide

출처 및 근거

ORD 기록
ord-0e66ceb581544733b3ae21efff3a4b0e
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04014877

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