Hydrochloric Acid → 5-Isobutyl-4-methyl-pyridine-2-carboxylic acid hydrochloride

HRID 1908801Notes

Reaction equation

HRID 1908801 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:8][N:7]=1)=[O:5])C.[ClH:17]>>[ClH:17].[CH2:13]([C:9]1[C:10]([CH3:12])=[CH:11][C:6]([C:4]([OH:5])=[O:3])=[N:7][CH:8]=1)[CH:14]([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 670270295-Isobutyl-4-methyl-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 673876435-Isobutyl-4-methyl-pyridine-2-carboxylic acid hydrochloride

Procedure

A solution of 5-isobutyl-4-methyl-pyridine-2-carboxylic acid ethyl ester (1.27 g, 5.76 mmol) in 6 N aq. HCl (110 mL) is stirred at 65° C. for 48 h before the solvent is evaporated in vacuo. The remaining residue is suspended in DCM and filtered. The solid material is washed with additional DCM and dried under HV to give 5-isobutyl-4-methyl-pyridine-2-carboxylic acid hydrochloride (1.05 g) as a white solid; LC-MS: tR=0.59 min; [M+1]+=194.28; 1H NMR (D6-DMSO): δ 0.90 (d, J=6.3 Hz, 6H), 1.85-1.96 (m, 1H), 2.69 (d, J=7.0 Hz, 2H), 8.18 (s, 1H), 8.58 (s, 1H), 11.80 (s br, 1H).

Workup

  1. customis evaporated in vacuo
  2. filtrationfiltered
  3. washThe solid material is washed with additional DCM
  4. customdried under HV

Sources & evidence

ORD record
ord-9627f544bcc94e4d9c022d7091b9d91c
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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