Hydrochloric Acid → 2-Methoxy-6-(trifluoromethyl)isonicotinic acid

HRID 878231ノート

反応式

HRID 878231 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1)[C:5]([OH:7])=[O:6].[CH3:15][OH:16].C[O-].[Na+].Cl>CCOC(C)=O>[CH3:15][O:16][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1)[C:5]([OH:7])=[O:6]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 112183892-Chloro-6-(trifluoromethyl)pyridine-4-carboxylic acid

生成物 1

HCID 706631682-Methoxy-6-(trifluoromethyl)isonicotinic acid収率 90.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-chloro-6-(trifluoromethyl)isonicotinic acid (0.15 g, 665 μmol, prepared according to F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2004, 18, 3793-3798) in methanol (2 mL) sodium methoxide (79.0 mg, 1.46 mmol) was added and the reaction refluxed for 5 hours. Another 287 mg (5.32 mmol) sodium methoxide was added and the white suspension was stirred at reflux temperature overnight. After 23 hours the suspension was allowed to cool to room temperature and was poured on saturated 1M HCl solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed once with brine, dried over MgSO4, filtered and evaporated to give the desired compound as a colorless solid (0.133 g; 90%). MS (ESI): m/z=220.02 [M−H]−.

後処理

  1. temperaturethe reaction refluxed for 5 hours
  2. temperatureat reflux temperature overnight
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted twice with EtOAc
  5. washThe organic layers were washed once with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-4c621cb4f9d342bbb64dbda2aa5e085a
出典データセット
uspto-grants-2015_03
特許番号
US08987307B2

反応ノート

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