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

HRID 1605701Notes

Reaction equation

HRID 1605701 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-934dc10e52d34e0fb0d0b0b70e949cc8
Source dataset
uspto-grants-1976_04
Patent number
US03950528

Reaction notes

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