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

HRID 930464Notes

Reaction equation

HRID 930464 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>ClCCl>[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 (synthesized according to procedure described in WO2012095521; 4.18 g, 19.15 mmol) in dichloromethane (96 ml) was added TFA (Aldrich, 148 ml, 1915 mmol). The reaction mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated under reduced pressure and the residue was triturated with EtOAc. The yellow slurry was concentrated under reduced pressure. The residue was triturated with 30 mL of methyl tert-butyl ether (30 mL) and of hexanes (50 mL) to yield 5-cyano-3-methylpicolinic acid (2.91 g, 17.95 mmol, 94% yield) as yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was triturated with EtOAc
  3. concentrationThe yellow slurry was concentrated under reduced pressure
  4. customThe residue was triturated with 30 mL of methyl tert-butyl ether (30 mL) and of hexanes (50 mL)

Sources & evidence

ORD record
ord-a27e4c270ad54d169bb607bf17bf96ec
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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