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

HRID 1402349Notes

Reaction equation

HRID 1402349 reaction equation
[NH:1]([CH2:3][CH2:4][OH:5])[NH2:2].[CH3:6][C:7]([CH3:14])([CH3:13])[C:8](=O)[CH2:9][C:10]#[N:11].Cl>CCO>[NH2:11][C:10]1[N:1]([CH2:3][CH2:4][OH:5])[N:2]=[C:8]([C:7]([CH3:14])([CH3:13])[CH3:6])[CH:9]=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 101%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydrazino-ethanol (2.98 mL, 44.0 mmol) was added to a stirred solution of 4,4-dimethyl-3-oxo-pentanenitrile (5.0 g, 40.0 mmol) in EtOH (IMS grade, 40 mL) at RT followed by concentrated HCl (0.4 mL). The reaction mixture was heated at reflux temperature for 18 h then cooled and concentrated in vacuo. The resultant residue was triturated with pentane to give the title compound (7.4 g, quantitative) as a yellow solid. LCMS (Method 3): Rt 0.81 min, m/z 184 [MH+].

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 18 h
  3. temperaturethen cooled
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was triturated with pentane

Sources & evidence

ORD record
ord-58955ea1ff384764bb1b272c823e42e6
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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