Methyl 3-aminocrotonate → 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 483195ノート

反応式

HRID 483195 の反応式
[F:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:13]/[C:14](/[CH3:20])=[CH:15]\[C:16]([O:18][CH3:19])=[O:17].[C:21]([O:27][CH2:28][CH2:29][N:30]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:31])(=[O:26])[CH2:22][C:23]([CH3:25])=O>CC(O)C>[CH3:25][C:23]1[NH:13][C:14]([CH3:20])=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=2[F:1])[C:22]=1[C:21]([O:27][CH2:28][CH2:29][N:30]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:31])=[O:26]

参加物

5

反応物 3

HCID 643918Methyl 3-aminocrotonateHCID 104873252-Fluoro-3-nitrobenzaldehydeHCID 117768292-(Benzylmethylamino)ethyl acetoacetate

生成物 1

HCID 104585422-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate収率 50.7%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A mixture of 330 mg of 2-fluoro-3-nitrobenzaldehyde, 252 mg of methyl 3-aminocrotonate and 506 mg of 2-(N-benzyl-N-methylamino)ethyl acetoacetate in 2 ml of 2-propanol was refluxed for 12 hours, and then the solvent was distilled off in vacuo. The residue was purified by the method of a column chromatography on silica gel to provide 492 mg of the desired compound (104).

後処理

  1. temperaturewas refluxed for 12 hours
  2. distillationthe solvent was distilled off in vacuo
  3. customThe residue was purified by the method of a column chromatography on silica gel

出典と根拠

ORDレコード
ord-ea62279ae4f04ee9af0ad9ccf5f23c39
出典データセット
uspto-grants-1986_03
特許番号
US04578395

反応ノート

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