Hydrochloric Acid → (2E)-3-[1-benzyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl]acrylic acid

HRID 30630Notes

Reaction equation

HRID 30630 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:11](/[CH:20]=[CH:21]/[C:22]([O:24]CC)=[O:23])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=C(/C=C/C(OCC)=O)C(C2C=CC(F)=CC=2)=N1)C1C=CC=CC=1.[OH-].[Na+].Cl>CO>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)=[C:11](/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86602514ethyl (2E)-3-[1-benzyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl]acrylateHCID 86602515HCID 86602515, compound

Product 1

HCID 69208840(2E)-3-[1-benzyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl]acrylic acidYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the mixture (4.0 g) of ethyl (2E)-3-[1-benzyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl]acrylate and ethyl (2E)-3-[1-benzyl-3-(4-fluorophenyl)-1H-pyrazol-4-yl]acrylate produced in Reference Example 32, a 2N aqueous sodium hydroxide solution (11 ml) and methanol (20 ml) was stirred at 60° C. for 14 hrs. 1N Hydrochloric acid (22 ml) was poured into the reaction mixture. The precipitated solids were collected by filtration, washed with water and isopropyl ether and dried with airflow to give a mixture (3.5 g, 95%) of (2E)-3-[1-benzyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl]acrylic acid and (2E)-3-[1-benzyl-3-(4-fluorophenyl)-1H-pyrazol-4-yl]acrylic acid as a powder.

Workup

  1. customproduced in Reference Example 32
  2. filtrationThe precipitated solids were collected by filtration
  3. washwashed with water and isopropyl ether
  4. customdried with airflow

Sources & evidence

ORD record
ord-9f1e8276727b43adb184684a1d10c17e
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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