2-Chloro-6-methylpyridine-4-carboxylic acid → 2-Chloro-6-methyl-isonicotinic acid tert-butyl ester

HRID 2354063Notes

Reaction equation

HRID 2354063 reaction equation
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([CH3:25])[N:24]=1)C(O)=O>C1(C)C=CC=CC=1>[C:11]([O:10][C:6](=[O:5])[C:18]1[CH:22]=[C:23]([CH3:25])[N:24]=[C:16]([Cl:15])[CH:17]=1)([CH3:12])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 1412092-Chloro-6-methylpyridine-4-carboxylic acidHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine

Product 1

HCID 860403662-Chloro-6-methyl-isonicotinic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

N,N-dimethylformamide-di-tert.-butyl-acetal (19 mL, 80 mmol) is added during 40 min to a hot (65° C., flask temperature) suspension of 2-chloro-6-methyl-isonicotinic acid (3.40 g, 19.8 mmol) in dry toluene (100 mL). The clear orange solution is stirred at 80° C. for 48 h, cooled to r.t. and diluted with toluene (100 mL). The solution is washed with water (2×40 mL), sat. aq. NaHCO3 (3×30 mL) and sat. aq. NaCl (25 mL), dried (Na2SO4), filtered and evaporated. The residue is purified by FC (SiO2, CH2Cl2-MeOH) to provide the title compound.

Workup

  1. temperaturecooled to r.t.
  2. washThe solution is washed with water (2×40 mL), sat. aq. NaHCO3 (3×30 mL) and sat. aq. NaCl (25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by FC (SiO2, CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-1a255b82ff9b4afe97b1df5975fd20d5
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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