Methyl iodide → HCID 54155695, compound

HRID 1414352Notes

Reaction equation

HRID 1414352 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:9]([NH2:26])[NH:8][C:7]=1[NH2:27])=[O:5])[CH3:2].[CH3:28]C[O-].[Na+].CI>C(O)C>[CH2:24]([O:23][C:21]([C:10]1([CH3:28])[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:7]([NH2:27])[N:8]=[C:9]1[NH2:26])=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 12448674HCID 12448674, compound

Product 1

HCID 54155695HCID 54155695, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 37.5 g of 2,6-diamino-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester and 6.8 g of sodium ethylate in 500 ml of ethanol was treated with 15 g of methyl iodide at the boil. After a further 60 minutes under reflux, the mixture was concentrated by distillation. The residue is taken up in 300 ml of chloroform and extracted by shaking twice with 100 ml of water, and the organic phase is concentrated. Recrystallization of the residue from ethanol gave 2,6-diamino-3-methyl-4-(3'-nitrophenyl)-3,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester of melting point 142°C (18 g, 41.5% of theory).

Workup

  1. temperatureAfter a further 60 minutes under reflux
  2. concentrationthe mixture was concentrated by distillation
  3. extractionextracted
  4. concentrationthe organic phase is concentrated
  5. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-c42d04f381dd4d7b9bfd0634bb941784
Source dataset
uspto-grants-1977_01
Patent number
US04001252

Reaction notes

Loading…