Sodium → Diethyl 2-amino-6-(fluoromethyl)-1,4-dihydro-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

HRID 364958Notes

Reaction equation

HRID 364958 reaction equation
[F:1][CH2:2][C:3](=O)[C:4](=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.[NH2:22][C:23]([NH2:30])=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].[Na]>C(O)C>[NH2:22][C:23]1[NH:30][C:3]([CH2:2][F:1])=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:24]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 124946853,3-Diamino-acrylic acid ethyl ester hydrochlorideHCID 54292052Ethyl 4-fluoro-2-(3-nitrophenylmethylene)-3-oxobutanoate

Product 1

HCID 20238658Diethyl 2-amino-6-(fluoromethyl)-1,4-dihydro-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethyl 4-fluoro-2-(3-nitrophenylmethylene)-3-oxobutanoate (0.6 g, 2.1 mmoles) and ethyl 3,3-diamino-2-propenoate hydrochloride (0.34 g, 12.0 mmoles) were heated at reflux in ethanol (10 ml) and a solution of sodium (0.05 g) in ethanol (5 ml) was added over one hour. The resulting solution was heated at reflux for a further 10 minutes and then filtered hot. The ethanolic solution was evaporated to dryness in vacuo and the resulting solid triturated with 2-propanol. The resulting solid was chromatographed on silica eluting with ether/petroleum ether (60°-80°) mixtures to give pure title compound, mp 177°-8°.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for a further 10 minutes
  3. filtrationfiltered hot
  4. customThe ethanolic solution was evaporated to dryness in vacuo
  5. customthe resulting solid triturated with 2-propanol
  6. customThe resulting solid was chromatographed on silica eluting with ether/petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-c5769b99291e47f2b68bda13b3329843
Source dataset
uspto-grants-1986_08
Patent number
US04607041

Reaction notes

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