Hydrochloric Acid → 1-(2-Hydroxy-1-phenylethyl)-1H-pyrazole-4-carboxylic acid

HRID 928382Notes

Reaction equation

[OH:1][CH2:2][CH:3]([N:10]1[CH:14]=[C:13]([C:15]([O:17]CC)=[O:16])[CH:12]=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].Cl>CCO>[OH:1][CH2:2][CH:3]([N:10]1[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[N:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 1-(2-hydroxy-1-phenylethyl)-1H-pyrazole-4-carboxylate (110 mg, 0.423 mmol) in EtOH (2 ml) was treated with NaOH (2N, 0.634 ml, 1.268 mmol) and heated to 90° C. for 30 min. The reaction mixture was acidified with 1N HCl, and all volatiles were removed in vacuo. The remaining residue was suspended in MeOH (10 ml) and filtered. Concentration of the filtrate afforded the title compound. LCMS RtM=1.58 min, [M+H]+=233.2.

Workup

customall volatiles were removed in vacuo
filtrationfiltered

Sources & evidence

ORD record: ord-5de70db8c77b4f6eb6c20a84e8babd3c
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290485B2

Reaction notes

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