Methylhydrazine → HCID 178488709, compound

HRID 628532Notes

Reaction equation

HRID 628532 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([CH3:16])[CH:9]=1)=O)C.[CH3:18][NH:19][NH2:20]>C1(C)C=CC=CC=1>[OH:3][C:4]1[N:19]([CH3:18])[N:20]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([CH3:16])[CH:9]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 21243218Ethyl 3-(4-methoxy-3-methylphenyl)-3-oxopropanoate

Product 1

HCID 178488709HCID 178488709, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, to a mixture of 3-(4-methoxy-3-methyl-phenyl)-3-oxo-propionic acid ethyl ester (described in Reference Preparation example 89) 14.8 g and toluene 100 ml was added N-methyl hydrazine 29 g, and the resulting mixture was stirred for twelve hours. The toluene was distilled off. At room temperature, to the reaction mixture was added water 100 ml and the resulting mixture was acidified with 10% aqueous hydrochloric acid solution and was stirred for three hours. The precipitates were filtered and were washed with water 400 ml and ethyl acetate 500 ml, and then were dried under reduced pressure to give 5-hydroxy-3-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole 9.3 g.

Workup

  1. distillationThe toluene was distilled off
  2. additionAt room temperature, to the reaction mixture was added water 100 ml
  3. stirringwas stirred for three hours
  4. filtrationThe precipitates were filtered
  5. washwere washed with water 400 ml and ethyl acetate 500 ml
  6. customwere dried under reduced pressure

Sources & evidence

ORD record
ord-aefca471f2ed4c7198f8c8a9df217573
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

Loading…