Potassium Hydroxide → 5-Cyclopentyloxy-6-methoxynicotinic acid

반응식

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

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실험 절차

A solution of potassium hydroxide (168 mg) in water (1 mL) is added to a solution of methyl 5-cyclopentyloxy-6-methoxynicotinoate (250 mg) in methanol (3 mL) and the mixture stirred for 4 hours then allowed to stand at room temperature overnight. The mixture is concentrated, the residue dissolved in water and the mixture adjusted to pH 6 by the addition of concentrated hydrochloric acid. The mixture is extracted with ethyl acetate, the extracts dried (MgSO4) and concentrated to give a cream solid. The solid is dried at 100° C. to give 5-cyclopentyloxy-6-methoxynicotinic acid (140 mg), m.p. 191-2° C. [Elemental analysis: C, 60.7; H, 6.43; N, 5.78%. calculated: C, 60.75; H, 6.37; N, 5.90%.].