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3-Nitrobenzaldehyde → Methyl 2,6-dimethyl-4-(3-nitrophenyl)-5-diisopropoxyphosphinyl-1,4-dihydropyridine-3-carboxylate

HRID 485076
ノート
印刷プレビュー

反応式

HRID 485076 の反応式
[CH2:1]([P:5](=[O:14])([O:10][CH:11]([CH3:13])[CH3:12])[O:6][CH:7]([CH3:9])[CH3:8])[C:2]([CH3:4])=O.[NH2:15]/[C:16](/[CH3:22])=[CH:17]\[C:18]([O:20][CH3:21])=[O:19].[N+:23]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH:29]=O)([O-:25])=[O:24].C(O)(=O)C.N1CCCCC1>C(O)(C)C>[CH3:22][C:16]1[NH:15][C:2]([CH3:4])=[C:1]([P:5]([O:10][CH:11]([CH3:13])[CH3:12])([O:6][CH:7]([CH3:9])[CH3:8])=[O:14])[CH:29]([C:28]2[CH:31]=[CH:32][CH:33]=[C:26]([N+:23]([O-:25])=[O:24])[CH:27]=2)[C:17]=1[C:18]([O:20][CH3:21])=[O:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 9793820Piperidine, acetateHCID 12616936Diisopropyl acetonylphosphonate

生成物 1

HCID 13363673Methyl 2,6-dimethyl-4-(3-nitrophenyl)-5-diisopropoxyphosphinyl-1,4-dihydropyridine-3-carboxylate収率 34.7%

試薬・触媒・溶媒 1

HCID 3776
Isopropanol
溶媒

実験手順

A mixture of 2.44 grams of diisopropyl acetonylphosphonate, 1.15 grams of methyl 3-aminocrotonate, and 1.51 grams of m-nitrobenzaldehyde was dissolved in 10 ml of isopropanol, then 290 mg of piperidine acetate was added thereto, and the mixture was heated to reflux for sixteen hours with stirring. The reaction solution was concentrated in vacuo, to the residue was added ether, the resulting crystals were collected by filtration, washed with ether and then with water, dried, and recrystallized from ethyl acetate to afford 1.57 grams (yield 34%) of methyl 2,6-dimethyl-4-(3-nitrophenyl)-5-diisopropoxyphosphinyl-1,4-dihydropyridine-3-carboxylate, melting point 205°-7° C.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for sixteen hours
  3. concentrationThe reaction solution was concentrated in vacuo, to the residue
  4. additionwas added ether
  5. filtrationthe resulting crystals were collected by filtration
  6. washwashed with ether
  7. dry with materialwith water, dried
  8. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-5e7b399ae93040c0a64d3db56cffb65e
出典データセット
uspto-grants-1985_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04535073

反応ノート

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