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 1087642Notes

Reaction equation

HRID 1087642 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3cea739d2eed43b3a439a39870a2818c
Source dataset
uspto-grants-1991_07
Patent number
US05036059

Reaction notes

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