Trifluoroacetic acid → 5-Cyano-3-methylpyridine-2-carboxylic acid

HRID 627680Notes

Reaction equation

HRID 627680 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH3:16])[C:6]([C:9]([O:11]C(C)(C)C)=[O:10])=[N:7][CH:8]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH3:16])[C:6]([C:9]([OH:11])=[O:10])=[N:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 666658265-Cyano-3-methyl-pyridine-2-carboxylic acid tert-butyl ester

Product 1

HCID 666658465-Cyano-3-methylpyridine-2-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-cyano-3-methylpicolinate (4.18 g, 19.15 mmol) in DCM (96 ml) was added TFA (148 ml, 1915 mmol), and the brown solution was stirred at RT for 2 h. The reaction mixture was concentrated. To the brown red residue was added EtOAc and it changed into a yellow slurry. It was concentrated again and dried on high vacuum. The reaction was triturated with 30 mL of MTBE and 50 ml of hexanes to yield 5-cyano-3-methylpicolinic acid (2.91 g, 17.95 mmol, 94% yield) as yellow solid. MS m/z=163.2 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionTo the brown red residue was added EtOAc and it
  3. concentrationIt was concentrated again
  4. customdried on high vacuum
  5. customThe reaction was triturated with 30 mL of MTBE and 50 ml of hexanes

Sources & evidence

ORD record
ord-df149db85ceb42ad84ae5666f2f543b6
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

Loading…