Benzyl Bromide → HCID 54393443, compound

HRID 1414351Notes

Reaction equation

HRID 1414351 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].CC[O-].[Na+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(O)C>[CH2:1]([O:3][C:4]([C:6]1([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[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 7498Benzyl BromideHCID 2723922Sodium ethoxideHCID 3779431HCID 3779431, compound

Product 1

HCID 54393443HCID 54393443, 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 17.1 g of benzyl 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-benzyl-6-methyl-4-(3'-nitrophenyl)-3,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester of melting point 208°C (29.4 g, 63% 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-f79258ae58e04ac5aba295ce6b6a301e
Source dataset
uspto-grants-1977_01
Patent number
US04001252

Reaction notes

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