Ethanol → HCID 69034876, compound

HRID 1930366Notes

Reaction equation

HRID 1930366 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([CH3:17])([CH3:16])[C:14]#N)[CH:3]=1.[OH-:18].[Na+].CC[OH:22]>>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([CH3:17])([CH3:16])[C:14]([OH:22])=[O:18])[CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 668758682-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropanenitrile

Product 1

HCID 69034876HCID 69034876, compoundYield 39%

Procedure

A solution of 2-(5-amino-1-phenyl-1 H-pyrazol-3-yl)-2-methyl-propionitrile (1.0 g, 7.4 mmol) and aq NaOH (2 M, 11 mL, 22 mmol) in EtOH (10 mL) was heated to 70° C. for 12 h. The reaction mixture was partitioned between ether and water and the aqueous solution was acidified with HCl to pH 4-5. The aqueous was extracted with EtOAc (3×50 mL) and the extracts were concentrated in vacuo to give crude 2-(5-amino-1-phenyl-1 H-pyrazol-3-yl)-2-methylpropanoic acid (0.7 g, 39% yield) which was used without further purification.

Workup

  1. customThe reaction mixture was partitioned between ether and water
  2. extractionThe aqueous was extracted with EtOAc (3×50 mL)
  3. concentrationthe extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-56db0198a1bd4b1b8c8927228b3a1614
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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