Ethanol → 3-(4-Chlorobenzyl)-1-methyl-1H-pyrazol-5-ylamine

HRID 401828Notes

Reaction equation

HRID 401828 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1.[CH3:14][NH:15][NH2:16].CCO>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH2:12])[N:15]([CH3:14])[N:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6061MethylhydrazineHCID 509888474-(4-Chlorophenyl)-3-oxobutanenitrile

Product 1

HCID 575512163-(4-Chlorobenzyl)-1-methyl-1H-pyrazol-5-ylamineYield 75%

Procedure

A solution of 4-(4-chlorophenyl)-3-oxo-butyronitrile (Preparation 96, 2.2 g, 11 mmol) and N-methylhydrazine (1.94 mL, 36.5 mmol) in EtOH (40 mL, 800 mmol) was heated at 100° C. in a 40 mL vial (the reaction was split into 2 equal batches). After 20 h, the reaction mixture was cooled to rt and concentrated in vacuo. The residue was purified on the Isco (40 g SiO2, hexanes to ethyl acetate) to afford the title compound as an off-white solid (1.83 g, 69%).

Workup

  1. customwas split into 2 equal batches)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified on the Isco (40 g SiO2, hexanes to ethyl acetate)

Sources & evidence

ORD record
ord-6da996e20958406ca918897d4c1b9787
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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