Ammonium hydroxide methanol → HCID 66958288, compound

HRID 1984380Notes

Reaction equation

HRID 1984380 reaction equation
[CH2:1]([C:3]1[N:7]([CH2:8][CH2:9][CH3:10])[N:6]=[C:5]([C:11]([O:13]CC)=O)[CH:4]=1)[CH3:2].[OH-].[NH4+:17].CO>>[CH2:1]([C:3]1[N:7]([CH2:8][CH2:9][CH3:10])[N:6]=[C:5]([C:11]([NH2:17])=[O:13])[CH:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 21894508Ammonium hydroxide methanolHCID 66958661HCID 66958661, compound

Product 1

HCID 66958288HCID 66958288, compound

Conditions

Temperature
125 °C

Procedure

Ethyl 5-ethyl-1-propyl-1H-pyrazole-3-carboxylate (13.0 g, 62 mmol) in a 4:1 mixture of concentrated ammonium hydroxide/methanol (50 mL) was heated at 125° C. for 18 hours in a pressure vessel. After cooling to ambient temperature, the contents of the vessel were poured into a flask and a precipitate formed immediately. The precipitate was isolated by filtration to yield 5.02 g of analytically pure 5-ethyl-1-propyl-1H-pyrazole-3-carboxamide as off-white crystals, mp 105-106° C. MS (APCI) m/z 182.1 (M+H)+; Anal. calcd for C9H15N3O: C, 59.64; H, 8.34; N, 23.19. Found: C, 59.59; H, 8.54; N, 23.39. An additional 0.50 g of product was obtained in the second crop from the filtrate.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. additionthe contents of the vessel were poured into a flask
  3. customa precipitate formed immediately
  4. customThe precipitate was isolated by filtration

Sources & evidence

ORD record
ord-f43b0decc2454fc4bee06a3927123fb6
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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