Sodium Hydroxide → methyl[1-(6-chloropyridazin-3-yl)-3-methyl-5-phenyl-1H-pyrazol-4-yl]acetate

HRID 2068481Notes

Reaction equation

[OH-].[Na+].[CH3:3][O:4][C:5](=[O:27])[CH2:6][CH:7]1[C:11](O)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]([C:19]2[N:20]=[N:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[N:9]=[C:8]1[CH3:26]>CO>[CH3:3][O:4][C:5](=[O:27])[CH2:6][C:7]1[C:8]([CH3:26])=[N:9][N:10]([C:19]2[N:20]=[N:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[C:11]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 20 °C

Procedure

0.111 g (2.772 mmol) of 2-molar aqueous sodium hydroxide solution was added to 0.200 g (0.554 mmol) of methyl[1-(6-chloropyridazin-3-yl)-5-hydroxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-4-yl]acetate in 8 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 0.207 g (99% of theory) of a brown wax-like solid, melting point 55° C.

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 0.207 g (99% of theory) of a brown wax-like solid, melting point 55° C.

Sources & evidence

ORD record: ord-96ac6f35c69e43759a3cdf9756ec0546
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08298994B2

Reaction notes

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