Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1) → Methyl 2-[5-amino-3-(3-pyridyl)pyrazol-1-yl]acetate

HRID 2205793Notes

Reaction equation

HRID 2205793 reaction equation
O=[C:2]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][C:4]#[N:5].Cl.[NH:13]([CH2:15][C:16]([O:18][CH2:19]C)=[O:17])[NH2:14]>CO>[NH2:5][C:4]1[N:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[N:14]=[C:2]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)HCID 157315343-Oxo-3-(3-pyridinyl)propanenitrile

Product 1

HCID 86717291Methyl 2-[5-amino-3-(3-pyridyl)pyrazol-1-yl]acetateYield 24.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-oxo-3-pyridin-3-ylpropane nitrile (1.31 g, 9 mmol), ethyl hydrazinoacetate hydrochloride (1.39 g, 9 mmol) in methanol (9 mL) was heated under microwave irradiation at 120° C. for 1 h. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (silica gel, ethyl acetate) yielding the title compound as a solid (510 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-f698412c32424cf3b6c748f54c7dcd33
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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