Sodium Hydroxide → [5-(3-Chlorophenyl)-3-methyl-1-pyridin-3-yl-1H-pyrazol-4-yl]acetic acid

HRID 888724Notes

Reaction equation

[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[N:14]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[N:13]=[C:12]([CH3:21])[C:11]=2[CH2:22][C:23]([O:25]C)=[O:24])[CH:7]=[CH:8][CH:9]=1>CO>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[N:14]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[N:13]=[C:12]([CH3:21])[C:11]=2[CH2:22][C:23]([OH:25])=[O:24])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 20 °C

Procedure

0.053 g (1.334 mmol) of 2 molar aqueous sodium hydroxide solution was added to 0.114 g (0.334 mmol) of methyl [5-(3-chlorophenyl)-3-methyl-1-pyridin-3-yl-1H-pyrazol-4-yl]acetate (see A1), and the mixture was stirred at 20° C. for 1 h. The methanol formed during the reaction 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 0.050 g (43% of theory) of a light-beige solid of melting point 163° C.

Workup

customwas 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 0.050 g (43% of theory) of a light-beige solid of melting point 163° C.

Sources & evidence

ORD record: ord-4ba4852abcb14a8a8b945b59793b39ff
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252723B2

Reaction notes

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