Sodium Carbonate → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid

HRID 548811Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester (3.1 g, 9.0 mmol) in ethanol (15 mL) was added aqueous sodium hydroxide (1 N, 27.5 mL). After heating at 60° C. for 30 min it was cooled to ambient temperature and and aqueous sodium carbonate (2 M, 50 mL) added. Addition of aqueous sodium hydroxide (1 M, 50 mL) was followed by extraction with tert-butylmethylether. The aqueous phase was acidified with aqueous hydrogen chloride (25%) to pH=2 and extracted with tert-butylmethylether and ethyl acetate. The combined organic layers were dried over sodium sulfate and concentration afforded the title compound (2.8 g, 100%) as a white solid after trituration from tert-butylmethylether. MS: m/e=309.3 [M−H]−.

Workup

temperaturewas cooled to ambient temperature
extractionwas followed by extraction with tert-butylmethylether
extractionextracted with tert-butylmethylether and ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate and concentration

Sources & evidence

ORD record: ord-7ab9868279f841f0ac99a7fd1ec387a2
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943619B2

Reaction notes

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