Acetic Acid → N-(5-Pyridin-4-yl-1H-pyrazol-3-yl)-acetamide

HRID 491529Notes

Reaction equation

HRID 491529 reaction equation
O=[C:2]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].[OH2:12].[NH2:13][NH2:14].[C:15](O)(=O)[CH3:16]>>[N:9]1[CH:10]=[CH:11][C:6]([C:2]2[NH:14][N:13]=[C:4]([NH:5][C:15](=[O:12])[CH3:16])[CH:3]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 157315353-Oxo-3-(pyridin-4-yl)propanenitrile

Product 1

HCID 67527634N-(5-Pyridin-4-yl-1H-pyrazol-3-yl)-acetamideYield 56%

Conditions

Temperature
70 °C

Procedure

To 3-oxo-3-pyridin-4-yl-propionitrile (10.0 g, 45 mmol) in 50 mL of acetic acid was added hydrazine monohydrate (1.59 g, 50 mmol) and the solution was heated to 70° C. overnight. The resulting white precipitate was collected and washed with diethyl ether and dried in vacuum to afford: 5.1 g (56% yield) of the title compound as an acetate salt. 1H NMR d6-DMSO: 10.90-10.60 (1H, vbs) 8.60-8.59 (2H, d), 7.71-7.70 (2H, d), 7.15-6.90 (1H, br s), 2.03 (3H, s), 1.87 (3H, s). FIA MS: MH+203.1, M−201.2.

Workup

  1. customThe resulting white precipitate was collected
  2. washwashed with diethyl ether
  3. customdried in vacuum
  4. customto afford

Sources & evidence

ORD record
ord-2d451983e7a2475ab4b8431cf32f390b
Source dataset
uspto-grants-2009_05
Patent number
US07531556B2

Reaction notes

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