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

HRID 485076
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인쇄 미리보기

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HRID 485076 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 3776
Isopropanol
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5e7b399ae93040c0a64d3db56cffb65e
출처 데이터셋
uspto-grants-1985_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04535073

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