2-Chloro-6-isobutylisonicotinic acid tert-butyl ester → 2-Chloro-6-isobutylisonicotinic acid hydrochloride

HRID 2040764Notes

Reaction equation

HRID 2040764 reaction equation
C([O:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([CH2:13][CH:14]([CH3:16])[CH3:15])[N:10]=[C:9]([Cl:17])[CH:8]=1)(C)(C)C>Cl.O1CCOCC1>[ClH:17].[Cl:17][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([CH2:13][CH:14]([CH3:16])[CH3:15])[N:10]=1)[C:6]([OH:18])=[O:5]

Participants

4

Reactant 1

HCID 866398762-Chloro-6-isobutylisonicotinic acid tert-butyl ester

Product 1

HCID 866398772-Chloro-6-isobutylisonicotinic acid hydrochlorideYield 102.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-chloro-6-isobutylisonicotinic acid tert.-butyl ester (1.70 g, 6.3 mmol) in 4 N HCl in dioxane (50 mL) is stirred at 60° C. for 30 h. The solvent is evaporated and the crude product is purified by MPLC on silica gel (heptane:EA gradient) to give 2-chloro-6-isobutylisonicotinic acid hydrochloride (0.81 g) as a beige resin; LC-MS: tR=0.89 min, [M+1]+=214.02.

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-b7cf0f4dde5b4adc993604e3630d18c3
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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