Hydrochloric Acid → 4-(Methoxymethyl)-6-(trifluoromethyl)pyridine-2-carboxylic acid

HRID 1426330노트

반응식

HRID 1426330 반응식
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:7]=[C:6]([C:14]#N)[CH:5]=1.[OH-:16].[Na+].[OH2:18].Cl>C(O)C>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:7]=[C:6]([C:14]([OH:18])=[O:16])[CH:5]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 696735024-(Methoxymethyl)-6-(trifluoromethyl)pyridine-2-carbonitrile

생성물 1

HCID 696732854-(Methoxymethyl)-6-(trifluoromethyl)pyridine-2-carboxylic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 4-(methoxymethyl)-6-(trifluoromethyl)pyridine-2-carbonitrile (0.36 g, 1.7 mmol, from Step C) in ethanol (20 mL) was added 1.0M sodium hydroxide in water (6.5 mL, 6.5 mmol) and the reaction was heated in an oil bath held at 90° C. for 4 hours. Upon cooling to room temperature, 1N HCl was added to achieve pH 2, and the product was extracted with ethyl acetate (3×). The combined extracts were dried over sodium sulfate, decanted and concentrated to afford a crystalline solid which was used without further purification. 1H NMR (300 MHz, CD3OD) δ 8.29 (s, 1H), 7.95 (s, 1H), 4.66 (s, 2H), 3.49 (s, 3H); 19F NMR (282 MHz, CD3OD) δ−69.56 (s); LCMS (M+H)+: 236.0.

후처리

  1. temperaturethe reaction was heated in an oil bath
  2. extractionthe product was extracted with ethyl acetate (3×)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. customdecanted
  5. concentrationconcentrated
  6. customto afford a crystalline solid which
  7. customwas used without further purification

출처 및 근거

ORD 기록
ord-70c070e8d747418088ffb47a6aac9a31
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933085B2

반응 노트

불러오는 중…