Ethyl cyanoacetate → 3-Amino-1-(4-bromobenzyl)-pyrazol-5one

HRID 617016Notes

Reaction equation

HRID 617016 reaction equation
[Na].C([O:4][C:5](=O)[CH2:6][C:7]#[N:8])C.[Br:10][C:11]1[CH:19]=[CH:18][C:14]([CH2:15][NH:16][NH2:17])=[CH:13][CH:12]=1>C(O)C>[NH2:8][C:7]1[NH:17][N:16]([CH2:15][C:14]2[CH:18]=[CH:19][C:11]([Br:10])=[CH:12][CH:13]=2)[C:5](=[O:4])[CH:6]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 5360545SodiumHCID 167731114-Bromobenzylhydrazine

Product 1

HCID 203672113-Amino-1-(4-bromobenzyl)-pyrazol-5one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

9.2 g of metallic sodium are dissolved in 200 ml of ethanol. A mixture of 25 g of cyanoacetic acid ethyl ester and 35 g of p-bromobenzylhydrazine in 50 ml of ethanol is then added at room temperature. The mixture is warmed to 60° C for 2 hours, the substance which was precipitated is filtered off and the filtrate is evaporated. The residue is taken up with water, the mixture is shaken with ether and the aqueous phase is acidified with dilute acetic acid. The crude product is purified by twice recrystallising it from alcohol.

Workup

  1. additionis then added at room temperature
  2. customthe substance which was precipitated
  3. filtrationis filtered off
  4. customthe filtrate is evaporated
  5. customThe crude product is purified
  6. customby twice recrystallising it from alcohol

Sources & evidence

ORD record
ord-6247ea53922c4f948c4a72a4f61b7b60
Source dataset
uspto-grants-1978_02
Patent number
US04076943

Reaction notes

Loading…