Methyl 3-aminocrotonate → Methyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate

HRID 1087642ノート

反応式

HRID 1087642 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH:7]=[C:8]([P:12]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][O:13]1)[C:9]([CH3:11])=O)([O-:3])=[O:2].[NH2:22]/[C:23](/[CH3:29])=[CH:24]\[C:25]([O:27][CH3:28])=[O:26]>C(O)(C)C>[CH3:29][C:23]1[NH:22][C:9]([CH3:11])=[C:8]([P:12]2(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:7]([C:6]2[CH:19]=[CH:20][CH:21]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:24]=1[C:25]([O:27][CH3:28])=[O:26]

参加物

4

反応物 2

HCID 643918Methyl 3-aminocrotonateHCID 540679512-(1-(3-Nitrobenzylidene)acetonyl)-2-oxo-1,3,2-dioxaphosphorinane

生成物 1

HCID 13604556Methyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate収率 49.9%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

Into 80 ml of isopropanol were dissolved 5.5 grams of 2-(1-(3-nitrobenzylidene)-acetonyl)-2-oxo-1,3,2-dioxaphosphorinane and 2.1 grams of methyl 3-aminocrotonate and the mixture was heated to reflux for 10 hours. After the reaction, the reaction solution was concentrated in vacuo, the residue was made crystallized by addition of ethyl acetate, and crystals separated out were collected by filtration. The crude crystals were recrystallized from ethyl acetate to give 3.6 grams of methyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate, m. p. 221°-3° C.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 10 hours
  3. customAfter the reaction
  4. concentrationthe reaction solution was concentrated in vacuo
  5. customthe residue was made crystallized by addition of ethyl acetate, and crystals
  6. customseparated out
  7. filtrationwere collected by filtration
  8. customThe crude crystals were recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-3cea739d2eed43b3a439a39870a2818c
出典データセット
uspto-grants-1991_07
特許番号
US05036059

反応ノート

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