o-(Trifluoromethyl)benzaldehyde → 1,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid methyl ester

HRID 2059088ノート

反応式

HRID 2059088 の反応式
[CH2:1]([N:8]1[CH2:13][C:12](O)=[CH:11][C:10](=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18](=[O:23])/[CH:19]=[C:20](\[NH2:22])/[CH3:21].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=O>C(O)C>[CH3:16][O:17][C:18]([C:19]1[CH:28]([C:27]2[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=2[C:25]([F:24])([F:34])[F:35])[C:11]2[C:10](=[O:15])[CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][C:12]=2[NH:22][C:20]=1[CH3:21])=[O:23]

参加物

5

反応物 3

HCID 123067o-(Trifluoromethyl)benzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 129006921-Benzyl-5-hydroxy-1,6-dihydropyridin-3(2H)-one

生成物 1

HCID 128184561,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 8.5 g. of 1-benzyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine, 4.75 g. of methyl-3-aminocrotonate (97%), 6.96 g. of o-trifluoromethylbenzaldehyde and 125 ml. of ethanol was refluxed for 2 hours. The mixture was filtered while hot and the filtrate was allowed to cool to room temperature. The solid was separated by filtration. Recrystallization from ethanol afforded the title compound, m.p. 225°-227° C.

後処理

  1. additionA mixture of 8.5 g
  2. filtrationThe mixture was filtered while hot and the filtrate
  3. customThe solid was separated by filtration
  4. customRecrystallization from ethanol

出典と根拠

ORDレコード
ord-4215ce00b30f4b349d48016b7d4e008c
出典データセット
uspto-grants-1982_03
特許番号
US04321384

反応ノート

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