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

HRID 1446652Notes

Reaction equation

HRID 1446652 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].[NH:10]([CH2:12][CH2:13][OH:14])[NH2:11].Cl>C(O)C.O.C(OCC)(=O)C>[NH2:6][C:5]1[N:10]([CH2:12][CH2:13][OH:14])[N:11]=[C:3]([C:2]([CH3:9])([CH3:8])[CH3:1])[CH:4]=1

Participants

7

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 66%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,4-dimethyl-3-oxo-pentanenitrile (5.0 g, 0.04 mol) in absolute ethanol (50 mL), add 2-hydrazino-ethanol (3 mL, 1.1 equiv.) and concentrated HCl (0.5 mL). Reflux the reaction for 4 hours then cool to room temperature and dilute with water and ethyl acetate. Wash the organics with water then saturated aqueous saturated sodium chloride then dry with magnesium sulfate, filter and concentrate in vacuo. Trituration from hexanes and dichloromethane gives a white solid (4.8 g, 66%). MS (ES), m/z 184 (M+1).

Workup

  1. temperatureReflux
  2. customthe reaction for 4 hours
  3. washWash the organics with water
  4. dry with materialsaturated aqueous saturated sodium chloride then dry with magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-3bfae7623a5943bfa49e2147f80891a1
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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