Hydrochloric Acid → 6-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid

HRID 1514697Notes

Reaction equation

HRID 1514697 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])=[N:6][CH:5]=1.O.[OH-].[Li+].Cl>C1COCC1.CO.O>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:13]2[C:12]([CH2:11][O:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:26])=[O:2])=[CH:5][N:6]=3)=[C:16]([CH2:17][OH:18])[O:15][N:14]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 667183126-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 667181326-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acidYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

6-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (3.0 g, 8.0 mmol) in THF (20 mL), methanol (5.2 mL) and water (19 mL) was treated with lithium hydroxide monohydrate (678 mg, 16.0 mmol) for 8 h at room temperature. Hydrochloride acid (1 N, 25 mL) and water (200 mL) were added to the reaction mixture. The precipitate was filtered off and washed with water and ethyl acetate to afford the title compound (2.67 g, 93%) as a white solid. MS: m/e=359.0 [M−H]−.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-7401a0083f00463faa78ff2ac7f77a2d
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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