Hydrochloric Acid → 3-fluoro-2-(1H-pyrazol-5-yl)benzoic acid

HRID 1193128Notes

Reaction equation

HRID 1193128 reaction equation
[F:1][C:2]1[C:3]([C:10]2[NH:14][N:13]=[CH:12][CH:11]=2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#N.[OH-:15].[Na+].Cl.C[OH:19]>>[F:1][C:2]1[C:3]([C:10]2[NH:14][N:13]=[CH:12][CH:11]=2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]([OH:19])=[O:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 671169283-fluoro-2-(1H-pyrazol-5-yl)benzonitrile

Product 1

HCID 670866093-fluoro-2-(1H-pyrazol-5-yl)benzoic acidYield 99%

Procedure

To 3-fluoro-2-(1H-pyrazol-5-yl)benzonitrile in MeOH (3 mL) was added 2M aq. NaOH (1 mL). The reaction was heated at reflux for 15 h, then cooled to rt, acidified with 1N aq. HCl to pH=1 and extracted with EtOAc to give (210 mg, 99%) of 3-fluoro-2-(1H-pyrazol-5-yl)benzoic acid which was used crude.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 15 h
  3. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-63935acda7ef4ca8aa135112a105a637
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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