Sodium Hydroxide → [3-Methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetic acid

HRID 888726Notes

Reaction equation

[OH-].[Na+].[CH3:3][C:4]1[C:8]([CH2:9][C:10]([O:12]C)=[O:11])=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:25]=2[CH3:26])[N:5]=1>CO>[CH3:3][C:4]1[C:8]([CH2:9][C:10]([OH:12])=[O:11])=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:25]=2[CH3:26])[N:5]=1

Participants

Conditions

Temperature: 20 °C

Procedure

0.100 g (2.489 mmol) of 2 molar aqueous sodium hydroxide solution was added to 0.200 g (0.498 mmol) of methyl [3-methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetate in 5.00 ml of methanol, and the mixture was stirred at 20° C. for 1 h. The methanol was removed under reduced pressure, and the residue was poured onto a mixture of 10 ml of water and 15 ml of dichloromethane. The aqueous phase was extracted with 15 ml of dichloromethane, acidified with concentrated hydrochloric acid (pH=3) and extracted three times with in each case 15 ml of dichloromethane. Drying of the combined organic phases and removal of the solvent under reduced pressure give 0.108 g (71% of theory) of a yellow solid of melting point 246° C.

Workup

customThe methanol was removed under reduced pressure
additionthe residue was poured onto a mixture of 10 ml of water and 15 ml of dichloromethane
extractionThe aqueous phase was extracted with 15 ml of dichloromethane
extractionextracted three times with in each case 15 ml of dichloromethane
customDrying of the combined organic phases and removal of the solvent under reduced pressure
customgive 0.108 g (71% of theory) of a yellow solid of melting point 246° C.

Sources & evidence

ORD record: ord-a531c57b56a4410ca1282e9efbb24737
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252723B2

Reaction notes

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