Methylhydrazine → 3-(3,5-dimethoxyphenyl)-1-methyl-1H-pyrazol-5-amine

HRID 402496Notes

Reaction equation

HRID 402496 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[CH2:12][C:13]#[N:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:16][NH:17][NH2:18]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]([NH2:14])[N:17]([CH3:16])[N:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 203875123-(3,5-Dimethoxyphenyl)-3-oxopropanenitrile

Product 1

HCID 431588653-(3,5-dimethoxyphenyl)-1-methyl-1H-pyrazol-5-amineYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(3,5-dimethoxyphenyl)-3-oxopropanenitrile (1.4 g, 6.82 mmol) and methyl hydrazine (0.54 ml, 10.23 mmol) in methanol (5 ml) was irradiated using a microwave at 160° C. for 0.25 h. The solution was evaporated under reduced pressure and the resulting crude product was purified by column chromatography (eluent 10% MeOH in CH2Cl2) to yield 1.3 g (82%) of the title compound. [1H-NMR (DMSO-d6, 360 MHz) δ 6.82 (d, 2H), 6.38 (t, 1H), 5.69 (2, 1H), 5.25 (s, 2H), 3.77 (s, 6H), 3.58 (s, 3H); UPLC-MS RtJ=0.69 min; [M+H]+=234.1]

Workup

  1. customat 160° C.
  2. customfor 0.25 h
  3. customThe solution was evaporated under reduced pressure
  4. customthe resulting crude product was purified by column chromatography (eluent 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-666e569ab6e9428db0280f9748eea9f6
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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