Hydrochloric Acid → 3-(5-Methylpyridin-2-yl)-5-(thiazol-2-yloxy)benzoic acid

HRID 1845287Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([O:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)[CH:17]=2)[C:11]([O:13]C)=[O:12])=[N:6][CH:7]=1.[OH-].[Li+].Cl>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([O:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)[CH:17]=2)[C:11]([OH:13])=[O:12])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 3-(5-methylpyridin-2-yl)-5-(thiazol-2-yloxy)benzoate (240 mg, 0.74 mmol) in tetrahydrofuran (6 mL) was added 2.5 M of aqueous lithium hydroxide solution (1.6 mL, 4.1 mmol). The reaction mixture was stirred at 60° C. overnight. The aqueous solution was acidified with 15% HCl (aq.) to pH=5-6, and extracted with EtOAc. The combined organic layers were concentrated in vacuo to get the title compound as a white solid. 1H NMR (CDCl3, 400 MHz): 8.77 (s, 1H), 8.70 (s, 1H), 8.08 (s, 1H), 8.04 (s, 1H), 7.71 (d, J=8.0 Hz, 1H), 7.64 (dd, J=8.0, 2.0 Hz, 1H), 7.25 (d, J=4.8 Hz, 1H), 6.85 (d, J=4.0 Hz, 1H), 2.41 (s, 3H).

Workup

extractionextracted with EtOAc
concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record: ord-db6f29517d5742bc8bf4704b51feddc2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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