Methyl iodide → HCID 54539259, compound

HRID 1414901Notes

Reaction equation

HRID 1414901 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:9]([CH3:23])[NH:8][C:7]=1[NH2:24])=[O:5])[CH3:2].[CH3:25]C[O-].[Na+].CI>C(O)C>[CH2:1]([O:3][C:4]([C:6]1([CH3:25])[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:9]([CH3:23])[N:8]=[C:7]1[NH2:24])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 12391088HCID 12391088, compound

Product 1

HCID 54539259HCID 54539259, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 33.0 g of 2-amino-6-methyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester and 6.8 g of sodium ethylate in 500 ml of ethanol is brought to the boil and treated with 15 g of methyl iodide. After boiling for a further 60 minutes under reflux, the mixture is concentrated by distillation and the residue is taken up in 300 ml of chloroform and extracted by shaking twice with 100 ml of water. Concentration of the organic phase and recrystallization from ethanol gives 18.6 g (54% of theory) of 2-amino-3,6-dimethyl-4-phenyl-3,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester of melting point 139° C.

Workup

  1. temperatureunder reflux
  2. concentrationthe mixture is concentrated by distillation
  3. extractionextracted
  4. customConcentration of the organic phase and recrystallization from ethanol

Sources & evidence

ORD record
ord-74a2f571c49d4267ad241036a043d3b6
Source dataset
uspto-grants-1977_01
Patent number
US04002762

Reaction notes

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