Hydrochloric Acid → HCID 66643575, compound

HRID 1807517Notes

Reaction equation

HRID 1807517 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:17][CH2:18][CH2:19][CH3:20])=[N:14][O:15][CH:16]=2)=[N:6][CH:5]=1.O.[OH-].[Li+].CO.Cl>C1COCC1.O>[CH2:17]([C:13]1[C:12]([CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[CH:5][N:6]=2)=[CH:16][O:15][N:14]=1)[CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 66643605HCID 66643605, compound

Product 1

HCID 66643575HCID 66643575, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6-(3-butyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (4.0 g, 13.8 mmol) in THF (25 mL) was added a solution of lithium hydroxide monohydrate (1.2 g, 27.6 mmol) in water (25 mL) and then methanol (7 mL) added and the resulting mixture stirred at room temperature for 2 h. The mixture was acidified to pH 1 with HCl (1 N, 80 mL) and the resulting mixture extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulphate, filtered and evaporated to afford the title compound (3.9 g, 100%) which was obtained as an off white solid. MS: m/e=277.1 [M+H]+.

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate
  2. washThe combined organic layers were then washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-11ca25294dee4fee95158773364c6cdb
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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