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

HRID 460884Notes

Reaction equation

HRID 460884 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-ce92e638c0bd4fd6a58ec88837c26c12
Source dataset
uspto-grants-1977_12
Patent number
US04061653

Reaction notes

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