Phenylhydrazine → 3-Cyclobutyl-1-phenyl-1H-pyrazol-5-amine

HRID 1918167Notes

Reaction equation

HRID 1918167 reaction equation
[CH:1]1([C:5](=O)[CH2:6][C:7]#[N:8])[CH2:4][CH2:3][CH2:2]1.[C:10]1([NH:16][NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[CH:1]1([C:5]2[CH:6]=[C:7]([NH2:8])[N:16]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:17]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 138611153-Cyclobutyl-3-oxopropanenitrile

Product 1

HCID 431589603-Cyclobutyl-1-phenyl-1H-pyrazol-5-amineYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A stirred mixture of 3-cyclobutyl-3-oxopropanenitrile (24.6 g, 0.20 mol) and phenylhydrazine (23.62 g, 0.20 mol) in ethanol (200 mL) was heated at 90° C. for 15 h. The reaction mixture was quenched with water and extracted with dichloromethane. The combined dichloromethane layers were dried over magnesium sulfate, concentrated under reduced pressure to give a solid which was triturated with a mixture of 10% petroleum ether in ethyl acetate, followed by trituration with diethyl ether to afford 3-cyclobutyl-1-phenyl-1H-pyrazol-5-amine (18.20 g, 43% over two steps) as a colorless solid. 1H NMR (400 MHz, DMSO-d6) δ 7.55-7.57 (m, 2H), 7.42-7.46 (m, 2H), 7.26 (m, 1H), 5.40 (s, 1H), 5.25 (s, 2H), 3.33 (m, 1H), 2.05-2.50 (m, 4H), 1.82-1.96 (m, 2H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined dichloromethane layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a solid which
  6. customwas triturated with a mixture of 10% petroleum ether in ethyl acetate

Sources & evidence

ORD record
ord-af9b4dd48b6744fc93411240b0d452a0
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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