Ethyl Bromide → HCID 53976044, compound

HRID 1414902Notes

Reaction equation

HRID 1414902 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]([CH3:26])[NH:8][C:7]=1[NH2:27])=[O:5])[CH3:2].[CH3:28][CH2:29][O-].[Na+].C(Br)C>C(O)C>[CH2:1]([O:3][C:4]([C:6]1([CH2:28][CH3:29])[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]([CH3:26])[N:8]=[C:7]1[NH2:27])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 2723922Sodium ethoxideHCID 3779431HCID 3779431, compound

Product 1

HCID 53976044HCID 53976044, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 37.4 g of 2-amino-6-methyl-4-(3'-nitrophenyl)-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 10.9 g of ethyl bromide. 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 gave 2-amino-3-ethyl-6-methyl-4-(3'-nitrophenyl)-3,4 -dihydropyridine-3,5-dicarboxylic acid diethyl ester of melting point 122°-3° C (16.5 g, 41% of theory).

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-39b340d9aa2f4b4ea5bd069be895f248
Source dataset
uspto-grants-1977_01
Patent number
US04002762

Reaction notes

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