Lithium Hydroxide → 1-PYRIDIN-2-YL-1H-PYRAZOLE-4-CARBOXYLIC ACID

HRID 1260331Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:10]=1)=[O:5])C.[OH-].[Li+]>C1COCC1.C(O)C>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:9]1[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

Pyridin-2-yl-1H-pyrazol-4-carboxylic acid ethyl ester (0.81 g, 3.73 mmol) was dissolved in a THF/ethanol (50 ml/10 ml) mixture, cooled to 0° C. and treated with lithium hydroxide (11.2 ml, 1N aqueous solution). The reaction mixture was allowed to warm-up to ambient temperature and subsequently stirred at that temperature for 7 h. The reaction mixture was extracted with dichloromethane (4×100 ml) and the combined organic phases were dried and evaporated to yield the product as white solid (0.68 g, 96%) which was used without any further purification.

Workup

temperatureto warm-up to ambient temperature
extractionThe reaction mixture was extracted with dichloromethane (4×100 ml)
customthe combined organic phases were dried
customevaporated

Sources & evidence

ORD record: ord-769cd1d08ae54c228b69cde1b7f701ba
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470820B2

Reaction notes

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