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

HRID 1526570Notes

Reaction equation

HRID 1526570 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 hexanes (50 mL) 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]+. Calculated for C8H6N2O2: 162.0

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 hexanes (50 mL)

Sources & evidence

ORD record
ord-dcd6aef9b42b4fbbb52521fdfb0a5bd9
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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