Ethanol → 3-Amino-4-methyl-1-(4-chlorobenzyl)-pyrazol-5-one

HRID 1438714Notes

Reaction equation

HRID 1438714 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][NH:7][NH2:8])=[CH:4][CH:3]=1.C(OC(=O)C(C)=CO[CH:18]([NH2:20])C)C.[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:34]([OH:36])[CH3:35]>>[NH2:20][C:18]1[NH:8][N:7]([CH2:6][C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:34](=[O:36])[C:35]=1[CH3:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 3015209(4-Chlorobenzyl)hydrazineHCID 86734339beta-Amino-beta-ethoxymethacrylic acid ethyl ester

Product 1

HCID 233343343-Amino-4-methyl-1-(4-chlorobenzyl)-pyrazol-5-one

Procedure

31.2 g of p-chlorobenzylhydrazine were added dropwise under nitrogen to a solution of 34.6 g of β-amino-β-ethoxymethacrylic acid ethyl ester and a pinch of p-toluenesulphonic acid in 200 ml of ethanol, whereupon the temperature rose from 21° C to 31° C. After standing overnight, the product which had precipitated was filtered off and recrystallized from ethanol.

Workup

  1. customrose from 21° C to 31° C
  2. customthe product which had precipitated
  3. filtrationwas filtered off
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-eaedfe87a9a14072a8d984a4805e981a
Source dataset
uspto-grants-1977_11
Patent number
US04056533

Reaction notes

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