Hydrochloric Acid → 2-Propyl-6-methylisonicotinic acid hydrochloride

HRID 1908717Notes

Reaction equation

HRID 1908717 reaction equation
C([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[CH:6]=1)C.[ClH:16]>>[ClH:16].[CH2:12]([C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([CH3:11])[N:8]=1)[C:4]([OH:15])=[O:3])[CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 669335582-Propyl-6-methylisonicotinic acid ethyl ester

Product 1

HCID 670271112-Propyl-6-methylisonicotinic acid hydrochloride

Procedure

A solution of 2-propyl-6-methylisonicotinic acid ethyl ester (2.30 g, 11.0 mmol) in 6 N aq. HCl (40 mL) is stirred at 65° C. for 24 h before it is cooled to rt and extracted with diethyl ether (2×50 mL). The aq. phase is evaporated and the residue is dried under HV to give 2-propyl-6-methylisonicotinic acid hydrochloride (2.0 g) as a colourless solid, LC-MS: tR=0.44 min; [M+1]+=180.09; 1H NMR (D6-DMSO): δ 8.02 (s, 1H), 7.99 (s, 1H), 3.04 (t, J=7.5 Hz, 2H), 2.78 (s, 3H), 1.82-1.72 (m, 2H), 0.93 (t, J=7.3 Hz, 3H).

Workup

  1. extractionextracted with diethyl ether (2×50 mL)
  2. customThe aq. phase is evaporated
  3. customthe residue is dried under HV

Sources & evidence

ORD record
ord-186c5e47b9404423be65b5e760910023
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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