Ethanolamine → Diethyl 2-methyl-4-(2-nitrophenyl)-6-(2-hydroxyethyl)iminomethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 614605ノート

反応式

HRID 614605 の反応式
[CH3:1][C:2]1[NH:3][C:4]([CH:27]=O)=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[NH2:29][CH2:30][CH2:31][OH:32].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:1][C:2]1[NH:3][C:4]([CH:27]=[N:29][CH2:30][CH2:31][OH:32])=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

参加物

6

反応物 4

HCID 700EthanolamineHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 13388352Diethyl 2-methyl-4-(2-nitrophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate

生成物 1

HCID 15737340Diethyl 2-methyl-4-(2-nitrophenyl)-6-(2-hydroxyethyl)iminomethyl-1,4-dihydropyridine-3,5-dicarboxylate収率 95.8%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture of diethyl 2-methyl- 4-(2-nitrophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate (1.1651 g), 2-aminoethanol (185 mg) and p-toluenesulfonic acid (catalytic amount) in dried benzene (20 ml) was refluxed under azeotropic dehydration for 1.5 hours. After cooling to room temperature, water was added to the resultant solution. The mixture was washed twice with water. The aqueous layer was extracted with diethyl ether and the extract was combined with the benzene solution. The mixed solution was dried over magnesium sulfate and then the solvent was removed from the solution to give viscous oil (1.2397 g) of diethyl 2-methyl-4-(2-nitrophenyl)-6-(2-hydroxyethyl)iminomethyl-1,4-dihydropyridine-3,5-dicarboxylate.

後処理

  1. temperaturewas refluxed under azeotropic dehydration for 1.5 hours
  2. washThe mixture was washed twice with water
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. dry with materialThe mixed solution was dried over magnesium sulfate
  5. customthe solvent was removed from the solution

出典と根拠

ORDレコード
ord-05fe89017f5b4f5a96669abfcf228c26
出典データセット
uspto-grants-1979_03
特許番号
US04145432

反応ノート

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