Hydrochloric Acid → 2,6-Dimethylisonicotinic acid hydrochloride

HRID 1908711Notes

Reaction equation

HRID 1908711 reaction equation
C([O:5][C:6](=[O:15])[C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([CH3:14])[CH:8]=1)(C)(C)C.[ClH:16]>C(O)(C)C>[ClH:16].[CH3:13][C:11]1[CH:12]=[C:7]([CH:8]=[C:9]([CH3:14])[N:10]=1)[C:6]([OH:15])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67027153tert-Butyl 2,6-dimethylisonicotinate

Product 1

HCID 533934312,6-Dimethylisonicotinic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2,6-dimethylisonicotinic acid tert.-butyl ester (2.37 g, 11.44 mmol) in 5 N HCl in isopropanol (40 mL) is stirred at 80° C. for 3 h. The solvent is evaporated and the crude product is purified by MPLC on silica gel (heptane:EA gradient) to give 2,6-dimethylisonicotinic acid hydrochloride as a beige resin; 1H NMR (CD3OD): δ 8.16 (s, 2H), 2.84 (s, 6H).

Workup

  1. customThe solvent is evaporated
  2. customthe crude product is purified by MPLC on silica gel (heptane:EA gradient)

Sources & evidence

ORD record
ord-53a182301d1b481dadce4cb9edebb3f5
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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