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2-(N-Benzyl-N-methylamino)ethyl 3-amino-2-butenoate → 2-(N-benzyl-N-methylamino)-ethyl 5-dimethoxyphosphinyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

HRID 485074
Notes
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Reaction equation

HRID 485074 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](/[CH3:38])=[CH:23]\[C:24]([O:26][CH2:27][CH2:28][N:29]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:30])=[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][CH2:27][CH2:28][N:29]([CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH3:30])=[O:25])=[C:22]([CH3:38])[NH:21][C:9]=1[CH3:11])=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 125291882-(N-Benzyl-N-methylamino)ethyl 3-amino-2-butenoateHCID 53986679Dimethyl 1-(3-nitrobenzylidene)-acetonylphosphonate

Product 1

HCID 133636712-(N-benzyl-N-methylamino)-ethyl 5-dimethoxyphosphinyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylateYield 21.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 3.42 grams of dimethyl 1-(3-nitrobenzylidene)-acetonylphosphonate and 3.13 grams of 2-(N-benzyl-N-methylamino)-ethyl 3-aminocrotonate was added 50 ml of isopropanol and the mixture was heated to reflux for four hours with stirring. The reaction mixture was concentrated in vacuo, the residue was dissolved in ethyl acetate, to this was added 5% hydrochloric acid solution followed by separation, chloroform was added the lower layer followed by separation, the chloroform layer was washed with 5% calcium carbonate solution and then with water, and dried. Chloroform was evaporated in vacuo, the residue was purified by subjecting to silica gel column chromatography (100 grams of silica gel being used; eluting solution is ethyl acetate), and the resulting crystals were recrystallized from a mixture of ethyl acetate and ether to give 1.28 grams (yield 20%) of 2-(N-benzyl-N-methylamino)-ethyl 5-dimethoxyphosphinyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate, pale yellow crystals, melting point 101°-3° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for four hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. additionto this was added 5% hydrochloric acid solution
  6. customfollowed by separation, chloroform
  7. additionwas added the lower layer
  8. customfollowed by separation
  9. washthe chloroform layer was washed with 5% calcium carbonate solution
  10. dry with materialwith water, and dried
  11. customChloroform was evaporated in vacuo
  12. customthe residue was purified
  13. customthe resulting crystals were recrystallized from a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-0f091b6f44bc495c9a5439d000075e70
Source dataset
uspto-grants-1985_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04535073

Reaction notes

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