4-Chloropyridine-2-carboxylic acid → HCID 21076072, compound

HRID 912702Notes

Reaction equation

HRID 912702 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].OS([O-])(=O)=O.[Na+]>C(O)CCC>[CH2:18]([O:19][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=1)[CH2:14][CH2:13][CH3:12]

Participants

6

Reactant 4

HCID 2308904-Chloropyridine-2-carboxylic acidHCID 516919Sodium BisulfateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 21076072HCID 21076072, compoundYield 182.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Conditions

Temperature
150 °C

Procedure

Sodium bis(trimethylsilyl)amide (28.8 g, 157 mmol) was added slowly to anhydrous n-butanol (52 mL). After 1 h, 4-chloro-pyridine-2-carboxylic acid (3.00 g, 19.1 mmol) was added and the reaction was heated to 150° C. for 3 h. Potassium bis(trimethylsilyl)amide (7.80 g, 39.2 mmol) in n-butanol (30 mL) was added to the reaction mixture and this was heated o.n. The mixture was cooled to r.t and pH was adjusted to 5 with 1N NaHSO4 solution. The mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, filtered and the solvent was removed in vacuo to give the title compound (3.40 g, 94% yield) as a solid.

Workup

  1. temperaturethis was heated o.n
  2. temperatureThe mixture was cooled
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5b54897a51db462ba9b19da6df43d859
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

Loading…