2-(n-Propoxy)ethyl 3-aminocrotonate → 2-n-Propoxyethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-diisopropoxyphosphinyl-1,4-dihydropyridine-3-carboxylate

HRID 485075Notes

Reaction equation

HRID 485075 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[CH:7]=[C:8]([P:12](=[O:21])([O:17][CH:18]([CH3:20])[CH3:19])[O:13][CH:14]([CH3:16])[CH3:15])[C:9]([CH3:11])=O)([O-:3])=[O:2].[NH2:25]/[C:26](/[CH3:37])=[CH:27]\[C:28]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][CH3:36])=[O:29]>C(O)(C)C>[CH3:37][C:26]1[NH:25][C:9]([CH3:11])=[C:8]([P:12]([O:17][CH:18]([CH3:20])[CH3:19])([O:13][CH:14]([CH3:16])[CH3:15])=[O:21])[CH:7]([C:6]2[CH:22]=[CH:23][CH:24]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:27]=1[C:28]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][CH3:36])=[O:29]

Participants

4

Reactant 2

HCID 125291902-(n-Propoxy)ethyl 3-aminocrotonateHCID 54197951Diisopropyl 1-(3-nitrobenzylidene)-acetonylphosphonate

Product 1

HCID 133636722-n-Propoxyethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-diisopropoxyphosphinyl-1,4-dihydropyridine-3-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5.1 grams of diisopropyl 1-(3-nitrobenzylidene)-acetonylphosphonate and 2.69 grams of 2-n-propoxyethyl 3-aminocrotonate was added to 20 ml of isopropanol and the mixture was heated to reflux for eight hours with stirring. The reaction mixture was evaporated in vacuo, to the residue was added ether to crystallize, the crystals were collected by filtration, and recrystallized from a mixture of ethyl acetate and ether to afford 5.38 grams of 2-n-propoxyethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-diisopropoxyphosphinyl-1,4-dihydropyridine-3-carboxylate, pale yellow crystals, melting point 125°-6° C. Yield 72%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for eight hours
  3. customThe reaction mixture was evaporated in vacuo, to the residue
  4. additionwas added ether
  5. customto crystallize
  6. filtrationthe crystals were collected by filtration
  7. customrecrystallized from a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-424b9c2d448a4e81b8df8e93230f9791
Source dataset
uspto-grants-1985_08
Patent number
US04535073

Reaction notes

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