Water → 5-amino-1-(2-phenylethyl)-1H-pyrazole-4-carboxylic acid

HRID 8300Notes

Reaction equation

HRID 8300 reaction equation
[OH:1]S(O)(=O)=O.[NH2:6][C:7]1[N:11]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=[CH:9][C:8]=1[C:20]#N.[OH2:22]>>[NH2:6][C:7]1[N:11]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=[CH:9][C:8]=1[C:20]([OH:1])=[O:22]

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 106085935-Amino-1-phenethyl-1H-pyrazole-4-carbonitrile

Product 1

HCID 220154975-amino-1-(2-phenylethyl)-1H-pyrazole-4-carboxylic acidYield 47%

Conditions

Temperature
60 °C

Procedure

A mixture of conc. H2SO4 (15 mL) and water (15 mL) was treated with 5-amino-1-(2-phenylethyl)-1H-pyrazole-4-carbonitrile (5.0 g, 23.6 mmol), heated at 60° C. for 1 h, poured into water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo, and recrystallised (EtOAc/MeOH) to give the title compound (2.53 g, 47%) as a cream solid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customrecrystallised (EtOAc/MeOH)

Sources & evidence

ORD record
ord-e8cbd27a036f4845829de860836a32e9
Source dataset
uspto-grants-2006_08
Patent number
US07087754B2

Reaction notes

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