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

HRID 1287874ノート

反応式

HRID 1287874 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

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 1 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.

後処理

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

出典と根拠

ORDレコード
ord-9102ee7178db4b24afd8420af9232718
出典データセット
uspto-grants-1976_10
特許番号
US03985882

反応ノート

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