Lithium Hydroxide → 2-(3-Methyl-1,2,4-oxadiazol-5-yl)isonicotinic acid

HRID 2281913Notes

Reaction equation

HRID 2281913 reaction equation
[OH-].[Li+].[CH3:3][C:4]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([O:14]C)=[O:13])[O:6][N:5]=1>C(O)C>[CH3:3][C:4]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([OH:14])=[O:13])[O:6][N:5]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67151212Methyl 2-(3-methyl-1,2,4-oxadiazol-5-yl)isonicotinate

Product 1

HCID 582525372-(3-Methyl-1,2,4-oxadiazol-5-yl)isonicotinic acidYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of lithium hydroxide (15 g, 0.35 mol), ethanol (500 mL) and methyl 2-(3-methyl-1,2,4-oxadiazol-5-yl)isonicotinate (52 g, 0.23 mol) were stirred at room temperature for 5 hours, then mixture was concentrated in vacuo. Water was added then extracted with ethyl acetate. The water layer was brought to pH 1.5 with aqueous 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was concentrated in vacuo to afford the title compound as a white solid (42 g). 1H NMR (300 MHz, DMSO-d6) δ ppm 14.08 (br s, 1H) 9.00-8.98 (m, 1 H) 8.50 (s, 1H) 8.09-8.07 (m, 1H), 2.46 (s, 3H).

Workup

  1. concentrationmixture was concentrated in vacuo
  2. additionWater was added
  3. extractionthen extracted with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-07d79fd7173c4245a49946f3f8d9feaa
Source dataset
uspto-grants-2015_09
Patent number
US09139587B2

Reaction notes

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