1,1,1-Trifluoro-2-propanol → 5-Cyano-6-(2,2,2-trifluoro-1-methylethoxy)nicotinic acid

HRID 1820971Notes

Reaction equation

HRID 1820971 reaction equation
[C:1]([C:3]1[C:4]([O:13][CH:14]([CH3:19])[C:15]([F:18])([F:17])[F:16])=[N:5][CH:6]=[C:7]([CH:12]=1)[C:8]([O:10]C)=[O:9])#[N:2].FC(F)(F)C(O)C.[OH-].[Na+]>CCOCC>[C:1]([C:3]1[C:4]([O:13][CH:14]([CH3:19])[C:15]([F:18])([F:17])[F:16])=[N:5][CH:6]=[C:7]([CH:12]=1)[C:8]([OH:10])=[O:9])#[N:2]

Participants

5

Reactant 3

HCID 97741,1,1-Trifluoro-2-propanolHCID 14798Sodium HydroxideHCID 68850684Methyl 5-cyano-6-(2,2,2-trifluoro-1-methylethoxy)nicotinate

Product 1

HCID 688518865-Cyano-6-(2,2,2-trifluoro-1-methylethoxy)nicotinic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 363 mg (1.32 mmol) of methyl 5-cyano-6-(2,2,2-trifluoro-1-methylethoxy)nicotinate (from Step C) and 5.0 mL of 1,1,1-trifluoro-2-propanol in 5.0 mL of Et2O was added 530 μL (2.65 mmol) of 5.0 N NaOH. After stirring at rt overnight, the mixture was diluted with Et2O (20 mL), washed with diluted HCl (2×10 mL), dried over Na2SO4, and concentrated to give 327 mg of the title compound: 1H NMR (500 MHz, CD3OD) δ 1.46 (d, J=6.4, 3H), 5.92 (m, 1H), 8.52 (d, J=2.1, 1H), 8.86 (d, J=2.0, 1H).

Workup

  1. washwashed with diluted HCl (2×10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-82c1288e14cc43db84205d03d73e97f7
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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