2-Chloro-6-(trifluoromethyl)nicotinonitrile → HCID 58873407, compound

HRID 1505221Notes

Reaction equation

HRID 1505221 reaction equation
Cl[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:14][O-:15].[Na+]>CO>[CH3:14][O:15][C:2]1[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:9]=1

Participants

4

Reactant 2

HCID 27784132-Chloro-6-(trifluoromethyl)nicotinonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 58873407HCID 58873407, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To 2-chloro-6-trifluoromethyl-nicotinonitrile (0.5 g, 2.4 mmol) in methanol (30 mL) was added sodium methylate in small portion (2 mol eq, 0.26 g). The reaction mixture was heated at 60° C. overnight. The solvent was distilled under reduced pressure and water was added to the residue. The aqueous solution was extracted with EtOAc (3×25 mL) and the organic phases were evaporated at reduced pressure to give 28c as a pale yellow oil (0.48 g, 2.33 mmol, 97% Yield). 1HNMR (DMSO, 200 MHz) δ 4.04 (s, 3H), 7.71 (d, 1H, J=6), 8.59 (d, 1H, J=6).

Workup

  1. distillationThe solvent was distilled under reduced pressure and water
  2. additionwas added to the residue
  3. extractionThe aqueous solution was extracted with EtOAc (3×25 mL)
  4. customthe organic phases were evaporated at reduced pressure

Sources & evidence

ORD record
ord-461cfd0ea51d49a0828e8e93572e682f
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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