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

HRID 485073Notes

Reaction equation

HRID 485073 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[CH:7]=[C:8]([P:12](=[O:17])([O:15][CH3:16])[O:13][CH3:14])[C:9]([CH3:11])=O)([O-:3])=[O:2].[NH2:21]/[C:22](/[CH3:28])=[CH:23]\[C:24]([O:26][CH3:27])=[O:25]>C(O)(C)C>[CH3:14][O:13][P:12]([O:15][CH3:16])([C:8]1[CH:7]([C:6]2[CH:18]=[CH:19][CH:20]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([CH3:28])[NH:21][C:9]=1[CH3:11])=[O:17]

Participants

4

Reactant 2

HCID 643918Methyl 3-aminocrotonateHCID 53986679Dimethyl 1-(3-nitrobenzylidene)-acetonylphosphonate

Product 1

HCID 10596880Methyl 5-dimethoxyphosphinyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylateYield 44.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 1.85 grams of dimethyl 1-(3-nitrobenzylidene)-acetonylphosphonate and 0.75 gram of methyl 3-aminocrotonate was added 25 ml of isopropanol and the mixture was heated to reflux for four hours with stirring. The reaction mixture was concentrated in vacuo, to the residue was added ether, the resulting crystals were collected by filtration, and recrystallized from ethyl acetate to afford 1.08 grams (yield 42%) of methyl 5-dimethoxyphosphinyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate, pale yellow crystals, melting point 221°-3° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for four hours
  3. concentrationThe reaction mixture was concentrated in vacuo, to the residue
  4. additionwas added ether
  5. filtrationthe resulting crystals were collected by filtration
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d22c3e6da8624db5a853704c4a307f39
Source dataset
uspto-grants-1985_08
Patent number
US04535073

Reaction notes

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