3-Nitrobenzaldehyde → 2-(4-Acetylaminobenzoyloxy)ethyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

HRID 542237

反応式

HRID 542237 の反応式
[C:1]([CH2:4][C:5]([O:7][CH2:8][CH2:9][O:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][CH:13]=1)=[O:6])(=O)[CH3:2].[NH2:23]/[C:24](/[CH3:31])=[CH:25]\[C:26]([O:28][CH2:29][CH3:30])=[O:27].[N+:32]([C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH:38]=O)([O-:34])=[O:33]>C(O)C>[CH3:2][C:1]1[NH:23][C:24]([CH3:31])=[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:38]([C:37]2[CH:40]=[CH:41][CH:42]=[C:35]([N+:32]([O-:34])=[O:33])[CH:36]=2)[C:4]=1[C:5]([O:7][CH2:8][CH2:9][O:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][CH:13]=1)=[O:6]

参加物

5

反応物 3

HCID 74493-NitrobenzaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 201512692-(4-Acetylaminobenzoyloxy)ethyl acetylacetate

生成物 1

HCID 201512802-(4-Acetylaminobenzoyloxy)ethyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate収率 46%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
-5 °C

実験手順

20 g (0.07 moles) of 2-(4-acetylaminobenzoyloxy)ethyl acetylacetate, 8.41 g (0.07 moles) of ethyl 3-aminocrotonate and 9.84 g (0.07 moles) of 3-nitrobenzaldehyde are heated under reflux in 65 ml of ethanol for 8 hours. The solvent is then evaporated, 15 ml of boiling methanol are added to the residue, the solution is discoloured with activated charcoal and cooled to -5° C. to obtain 2-(4-acetylaminobenzoyloxy)ethyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate with half a molecule of ethanol as yellow crystals melting--after recrystallisation in ethanol--at 157°-162° C. The yield is 46% of the theoretical yield.

後処理

  1. customThe solvent is then evaporated
  2. addition15 ml of boiling methanol are added to the residue

出典と根拠

ORDレコード
ord-3f96357e28524010b415e2a09d4494b8
出典データセット
uspto-grants-1987_04
特許番号
US04656181

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