Ethyl Acetate → 8,10a-Dihydro-7,9-dimethyl-6-oxo-6H-pyrano(3,2-b:5,4-c') dipyridine-10-carboxylic acid ethyl ester

HRID 1632955ノート

反応式

HRID 1632955 の反応式
[OH:1][C:2]1[C:3]([CH:8]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH3:19])[NH:11][C:10]([CH3:20])=[C:9]2[C:21]([O:23]CC)=O)=[N:4][CH:5]=[CH:6][CH:7]=1.N12CCCC=C1CCCCN2.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:17]([O:16][C:14]([C:13]1[CH:8]2[C:3]3=[N:4][CH:5]=[CH:6][CH:7]=[C:2]3[O:1][C:21](=[O:23])[C:9]2=[C:10]([CH3:20])[NH:11][C:12]=1[CH3:19])=[O:15])[CH3:18]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 9834010Diazabicyclo[5.4.0]undec-7-eneHCID 13374597Diethyl 1,4-dihydro-4-(3-hydroxypyridyl)-2,6-dimethyl-3,5-pyridine dicarboxylate

生成物 1

HCID 133745998,10a-Dihydro-7,9-dimethyl-6-oxo-6H-pyrano(3,2-b:5,4-c') dipyridine-10-carboxylic acid ethyl ester収率 55.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
140 °C

実験手順

Diethyl 1,4-dihydro-4-(3-hydroxypyridyl)-2,6-dimethyl-3,5-pyridine dicarboxylate (17.3 grams; 0.05 mole) was nearly dissolved in 250 ml toluene heated at 140° C. Diazabicyclo(5.4.0) undec-7-ene (8.3 grams; 8.2 ml; 0.05 mole) dissolved in 20 ml toluene was added and the reaction mixture refluxed for a period of 22 hours at 180° C. (bath temperature). The black solution was cooled and concentrated to afford 23.3 grams of a black paste. High pressure liquid chromatography (HPLC) using ethyl acetate yielded 8.3 grams of a yellow solid, m.p. 100°-150° C. Two recrystallizations from 2-propanol gave 4.5 grams (30%) of fluorescent yellow material, m.p. 150°-160° C.

後処理

  1. additionwas added
  2. temperaturethe reaction mixture refluxed for a period of 22 hours at 180° C. (bath temperature)
  3. temperatureThe black solution was cooled
  4. concentrationconcentrated
  5. customto afford 23.3 grams of a black paste

出典と根拠

ORDレコード
ord-48e17ef061194e6dad16d5023da9be4c
出典データセット
uspto-grants-1984_10
特許番号
US04478834

反応ノート

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