Trifluoroacetic acid → 3-Chloro-5-cyanopyridine-2-carboxylic acid

HRID 627686Notes

Reaction equation

HRID 627686 reaction equation
[Cl:1][C:2]1[C:3]([C:10]([O:12]C(C)(C)C)=[O:11])=[N:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:10]([OH:12])=[O:11])=[N:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867281412-Pyridinecarboxylic acid, 3-chloro-5-cyano-, 1,1-dimethylethyl ester

Product 1

HCID 508531763-Chloro-5-cyanopyridine-2-carboxylic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-chloro-5-cyanopicolinate (1.4 g, 3.23 mmol) in DCM (10.75 ml) was added TFA (25 ml, 323 mmol). The orange solution was stirred at RT for 1 hr. It was concentrated. Then the residue was passed through a PEAX column and the acid was eluted with 2% conc. HCl in MeOH (0.3 mL in 15 mL MeOH) to yield 3-chloro-5-cyanopicolinic acid (0.55 g, 3.01 mmol, 93% yield) as yellow solid. MS m/z=183 (M+H).

Workup

  1. concentrationIt was concentrated
  2. washthe acid was eluted with 2% conc. HCl in MeOH (0.3 mL in 15 mL MeOH)

Sources & evidence

ORD record
ord-e05e5fea18cc4b31880d716dc83428dd
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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