Diethyl (ethoxymethylene)malonate → ethyl 6,7-dihydro-9-(N,N-dimethylamino)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate

HRID 918163노트

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HRID 918163 반응식
[CH3:1][N:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]([CH3:14])[CH2:8][CH2:7]2)[CH3:3].C([O:17][CH:18]=[C:19]([C:25](OCC)=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])C.[OH-].[Na+]>O>[CH3:3][N:2]([C:4]1[CH:13]=[C:12]2[C:11]3[N:10]([CH:25]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:18]2=[O:17])[CH:9]([CH3:14])[CH2:8][CH2:7][C:6]=3[CH:5]=1)[CH3:1]

참가 물질

5

반응물 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 14798Sodium HydroxideHCID 214453526-quinolinamine, 1,2,3,4-tetrahydro-N,N,2-trimethyl-

생성물 1

HCID 21445355ethyl 6,7-dihydro-9-(N,N-dimethylamino)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate

시약·촉매·용매 1

HCID 962Water용매

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온도
120 °C

실험 절차

6-(N,N-Dimethylamino)-2-methyltetrahydroquinoline (25 g., 0.132 mole) is mixed with diethyl ethoxymethylenemalonate (28.4 g., 0.132 mole), and the mixture is heated at 120° C. for 3 hours. Polyphosphoric acid (200 g.) is added, and the solution is heated gradually to 120° C. with occasional stirring. The solution is maintained at 120° to 130° C. for one hour then poured into 500 ml. of water, with stirring. The solution is neutralized with 40 percent sodium hydroxide solution. The yellow product is separated by filtration and recrystallized from ethanol giving ethyl 6,7-dihydro-9-(N,N-dimethylamino)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate, m.p. 219°-222° C.

후처리

  1. temperaturethe solution is heated gradually to 120° C. with occasional stirring
  2. temperatureThe solution is maintained at 120° to 130° C. for one hour
  3. additionthen poured into 500 ml
  4. customThe yellow product is separated by filtration
  5. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-82f34e7c559946528a7ba5c55e279b74
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03969463

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