Hydrochloric Acid → 2-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)ethan-1-ol

HRID 572071Notes

Reaction equation

HRID 572071 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.[NH:11]([CH2:13][CH2:14][OH:15])[NH2:12]>C(O)C>[NH2:6][C:5]1[N:11]([CH2:13][CH2:14][OH:15])[N:12]=[C:3]([C:2]([CH3:9])([CH3:8])[CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80172-HydrazinoethanolHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 162278772-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)ethan-1-olYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,4-dimethyl-3-oxo-pentanenitrile (5.00 g, 40.0 mmol), concentrated HCl (0.1 mL), and 2-hydrazino ethanol (2.98 mL, 44.0 mmol) in ethanol (40 mL) was refluxed for 20 h. The reaction mixture was then concentrated in vacuo. The resulting oily solid was washed with cyclohexane (30 mL), and dissolved in MeOH (5 mL) and H2O (5 mL) and lyophilised to give the title compound as a white powder (7.13 g, 97%). LCMS (Method 3): Rt 0.43 min, m/z 184 [MH+].

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. washThe resulting oily solid was washed with cyclohexane (30 mL)
  3. dissolutiondissolved in MeOH (5 mL)

Sources & evidence

ORD record
ord-906bd3e6bdce41f2b495d779f6f3fdb4
Source dataset
uspto-grants-2015_05
Patent number
US09029373B2

Reaction notes

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