Reaction #48818

Reaction equation

2-Chloroacrylonitrile

N-isopropylhydrazine hydrochloride

potassium carbonate

→

title compound

Yield 58.0%

1-Isopropyl-1H-pyrazol-3-amine

Yield 58.0%

Solvents

water

Conditions

Workup

1. 1
   Temperaturebefore cooling back to RT
2. 2
   ExtractionThe aqueous layer was then extracted with ethyl acetate (5×30 mL)
3. 3
   Dryingthe combined organic layers were dried (MgSO4)
4. 4
   workup.ADDITIONtreated with activated charcoal
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   OtherThe residue was purified by chromatography
8. 8
   Washeluting with 67%-100% ethyl acetate in hexanes

Procedure

2-Chloroacrylonitrile (3.41 mL, 42.59 mmol) was added at RT to a stirring solution of N-isopropylhydrazine hydrochloride (4.71 g, 42.6 mmol), potassium carbonate (11.8 g, 85.2 mmol) in water (50 mL). The reaction was warmed to 45° C. for 4 hours before cooling back to RT. The aqueous layer was then extracted with ethyl acetate (5×30 mL) and the combined organic layers were dried (MgSO4), treated with activated charcoal, filtered and evaporated. The residue was purified by chromatography, eluting with 67%-100% ethyl acetate in hexanes, to afford the title compound (3.08 g, 58%) as a 6:1 mixture of authentic product to regioisomeric product as an oil. The material was used without further purification.

Source