Hydrochloric Acid → 2-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isonicotinic acid

HRID 1897062Notes

Reaction equation

HRID 1897062 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:5]=1.O.[OH-].[Li+].Cl>C1COCC1.O.CO>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]=1[CH2:11][O:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][N:7]=1)[C:3]([OH:24])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 684433292-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isonicotinic acid methyl ester

Product 1

HCID 684441282-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isonicotinic acidYield 89.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isonicotinic acid methyl ester (759 mg, 2.3 mmol) in THF (6.3 mL) was added a solution of lithium hydroxide monohydrate (196 mg, 4.7 mmol) in water (6.3 mL) and methanol (1.4 mL) added and the resulting mixture stirred at room temperature for 2 h. The mixture was acidified to pH 4 with HCl (25%, 3 drops and the resulting precipitate filtered off and dried to afford the title compound (641 mg, 88%) which was obtained as a white solid. MS: m/e=309.5 [M−H]−.

Workup

  1. additionadded
  2. filtrationthe resulting precipitate filtered off
  3. customdried

Sources & evidence

ORD record
ord-7ef745ba7fa24753854137974a5f8b74
Source dataset
uspto-grants-2013_08
Patent number
US08518974B2

Reaction notes

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