Sodium Hydroxide → [1-(6-Chloropyridazin-3-yl)-3-methyl-5-phenyl-1H-pyrazol-4-yl]acetic acid

HRID 2068482Notes

Reaction equation

[OH-].[Na+].C[O:4][C:5](=[O:26])[CH2:6][C:7]1[C:8]([CH3:25])=[N:9][N:10]([C:18]2[N:19]=[N:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CO>[Cl:24][C:21]1[N:20]=[N:19][C:18]([N:10]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]([CH2:6][C:5]([OH:26])=[O:4])[C:8]([CH3:25])=[N:9]2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 20 °C

Procedure

0.058 g (1.444 mmol) of 2-molar aqueous sodium hydroxide solution was added to 0.099 g (0.289 mmol) of methyl[1-(6-chloropyridazin-3-yl)-3-methyl-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 into 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 gave 0.052 g (54.7% of theory) of a brown wax-like solid.

Workup

customThe methanol was removed under reduced pressure
additionthe residue was poured into 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
customgave 0.052 g (54.7% of theory) of a brown wax-like solid

Sources & evidence

ORD record: ord-d36ab2cede2943ae9d71b6046240b9b9
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08298994B2

Reaction notes

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