Toluene → 14776-37-5

HRID 2309367Notes

Reaction equation

HRID 2309367 reaction equation
[C:1]([O:5]C)(=O)[CH2:2][CH3:3].[CH3:7][NH:8][NH2:9].[C:10]1(C)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH3:7][N:8]1[CH:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:2][C:1](=[O:5])[NH:9]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6061MethylhydrazineHCID 11124Methyl propionate

Product 1

HCID 9549014776-37-5

Procedure

20.5 g methyl propionate were dissolved in 150 ml toluene and 6.7 ml methyl hydrazine were added to the solution under ice cooling. After standing for 12 hours, the solution was evaporated. The residue was a mixture of 1-methyl-5-phenylpyrazolin-3-one and 2-methyl-5-phenylpyrazolin-3-one. This crude isomeric mixture was chromatographed on silica gel. Ether was used as elution agent, to which increasing quantities of methanol were added. From the eluate the non-polar 1-methyl-5-phenylpyrazolin-3-one was isolated. Melting point: 160°-161° C.; yield 6.3 g.

Workup

  1. customthe solution was evaporated
  2. additiona mixture of 1-methyl-5-phenylpyrazolin-3-one and 2-methyl-5-phenylpyrazolin-3-one
  3. customThis crude isomeric mixture was chromatographed on silica gel
  4. washEther was used as elution agent, to which
  5. temperatureincreasing quantities of methanol
  6. additionwere added

Sources & evidence

ORD record
ord-69aa77a7492b41af9d5d6e05fccce67d
Source dataset
uspto-grants-1987_09
Patent number
US04695566

Reaction notes

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