Hydrochloric Acid → 3-cyclopropyl-5-(difluoromethyl)-1H-pyrazole

HRID 1408526Notes

Reaction equation

HRID 1408526 reaction equation
[CH:1]1([C:4](=O)/[CH:5]=[C:6](\O)/[CH:7]([F:9])[F:8])[CH2:3][CH2:2]1.O.[NH2:13][NH2:14].Cl>C(O)C>[CH:1]1([C:4]2[NH:14][N:13]=[C:6]([CH:7]([F:9])[F:8])[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 23237111HCID 23237111, compound

Product 1

HCID 71474033-cyclopropyl-5-(difluoromethyl)-1H-pyrazoleYield 76.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Intermediate 62 (390 mg, 2.4 mmol) dissolved in ethanol (2 ml), added hydrazine hydrate (0.13 ml, 2.65 mmol) and HCl (0.18 ml). This mixture was refluxed for 3 h. After 3 h, ethanol was removed on rotavapour and work up (H2O/AcOEt) afforded the title compound (290 mg) which was used in the next step without further purification. 1H-NMR (δ ppm, CDCl3, 400 MHz): 12.96 (s, 1H), 6.84 (t, J 54.8, 1H), 6.15 (s, 1H), 1.95-1.87 (m, 1H), 0.99-0.91 (m, 2H), 0.74-0.66 (m, 2H).

Workup

  1. temperatureThis mixture was refluxed for 3 h
  2. customethanol was removed on rotavapour and work up (H2O/AcOEt)

Sources & evidence

ORD record
ord-6aa66397e2684a95b363c4ce6e33387f
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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