Potassium Hydroxide → 3-amino-N,N,1-trimethyl-1H-pyrazole-5-carboxamide

HRID 1971417Notes

Reaction equation

HRID 1971417 reaction equation
[OH-].[K+].Cl.NO.[CH3:6][N:7]([CH3:23])[C:8]([C:10]1[N:11]([CH3:22])[N:12]=[C:13]([N:15]2C(C)=CC=C2C)[CH:14]=1)=[O:9]>O.C(O)C>[CH3:6][N:7]([CH3:23])[C:8]([C:10]1[N:11]([CH3:22])[N:12]=[C:13]([NH2:15])[CH:14]=1)=[O:9]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 593947615-(2,5-Dimethyl-pyrrol-1-yl)-2-methyl-2H-pyrazole-3-carboxylic acid dimethylamide

Product 1

HCID 593947723-amino-N,N,1-trimethyl-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (1.1 g, 19.5 mmol) in water (30 mL) and ethanol (30 mL) is added to a slurry of hydroxylamine hydrochloride (2.7 g, 39 mmol) in ethanol (50 mL). 5-(2,5-dimethyl-pyrrol-1-yl)-2-methyl-2H-pyrazole-3-carboxylic acid dimethylamide (1.6 g, 6.5 mmol) is added and the mixture is refluxed for 48 hours. The contents of the flask are then concentrated under reduced pressure and the residue is suspended in DCM. The suspension is heated to reflux and then cooled down to room temperature, filtered and the filtrate is concentrated to give crude product. MS (ESI) m/z 169.3 (M+1).

Workup

  1. temperaturethe mixture is refluxed for 48 hours
  2. concentrationThe contents of the flask are then concentrated under reduced pressure
  3. temperatureThe suspension is heated
  4. temperatureto reflux
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated
  7. customto give crude product

Sources & evidence

ORD record
ord-b98017815f4d42fe9618c556338629ef
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

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