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

HRID 597521

反応式

HRID 597521 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
220 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0e66ceb581544733b3ae21efff3a4b0e
出典データセット
uspto-grants-1977_03
特許番号
US04014877

関連ノート

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