Ethanol → 2-(1-methyl-1H-imidazol-4-yl)pyridine-4-carboxylic acid

HRID 2277438Notes

Reaction equation

HRID 2277438 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=C(C#N)[CH:10]=[CH:9][N:8]=2)[N:4]=[CH:3]1.[OH-:15].[Na+].[CH3:17][CH2:18][OH:19]>>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:17]([C:18]([OH:15])=[O:19])[CH:10]=[CH:9][N:8]=2)[N:4]=[CH:3]1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 904075092-(1-Methylimidazol-4-yl)pyridine-4-carbonitrile

Product 1

HCID 862688822-(1-methyl-1H-imidazol-4-yl)pyridine-4-carboxylic acidYield 40%

Conditions

Temperature
90 °C

Procedure

A solution of 2-(1-methyl-1H-imidazol-4-yl)pyridine-4-carbonitrile (50 mg, 0.3 mmol) in EtOH (2 mL) was treated with 10N NaOH (0.5 ml) and stirred at 90° C. for 2 hrs. The reaction mixture was purified by prep-HPLC to afford the title compound (22 mg, 40%) as light pink solid. 1H NMR (400 MHz, DMSO-d6): δ 3.72 (3H, s), 7.57 (1H, d, J=5 Hz), 7.72 (1H, s), 7.76 (1H, s), 8.28 (1H, s), 8.63 (1H, d, J=4.9 Hz). [M+H] Calc'd for C10H9N3O2, 204. Found, 204.

Workup

  1. customThe reaction mixture was purified by prep-HPLC

Sources & evidence

ORD record
ord-85620edba3134e9fbda33c81f33c1dea
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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