Methanamine, N-methoxy-, hydrochloride (1:1) → N-Methoxy-N-methyl-6-(4-trifluoromethyl-phenyl)-nicotinamide

HRID 1669303노트

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HRID 1669303 반응식
CO[C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:6][CH:5]=1.Cl.[CH3:22][NH:23][O:24][CH3:25].C([Mg]Cl)(C)C>O1CCCC1>[CH3:25][O:24][N:23]([CH3:22])[C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=2)=[N:6][CH:5]=1

참가 물질

5

반응물 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 21936350Methyl 6-(4-(trifluoromethyl)phenyl)nicotinateHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 86620355N-Methoxy-N-methyl-6-(4-trifluoromethyl-phenyl)-nicotinamide수율 99.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-30 °C

실험 절차

6-(4-Trifluoromethyl-phenyl)-nicotinic acid methyl ester (20 g, 71.2 mmol) is dissolved into anhydrous tetrahydrofuran (TVF) (300 mL) and then cooled to −30° C. while stirring under nitrogen. N,O-dimethylhydroxylamine hydrochloride (10.4 g, 107 mmol) is then added to the solution in one portion. Isopropyl magnesium chloride (107 mL, 2M soln. in THF, 252 mmol) is slowly added to the cooled suspension over 2 h. After complete consumption of starting material, 30% solution of ammonium chloride is added with stirring. The reaction is diluted with diethyl ether, water, and extracted. The organic layer is collected and washed with cold water (2×) and brine. The solution is then dried over anhydrous sodium sulfate, filtered, and concentrated. The N-Methoxy-N-methyl-6-(4-trifluoromethyl-phenyl)-nicotinamide (22 g, 71 mmol) is obtained in purified form after flash column chromatography.

후처리

  1. customAfter complete consumption of starting material, 30% solution of ammonium chloride
  2. additionis added
  3. stirringwith stirring
  4. additionThe reaction is diluted with diethyl ether, water
  5. extractionextracted
  6. customThe organic layer is collected
  7. washwashed with cold water (2×) and brine
  8. dry with materialThe solution is then dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-32170527dd65416fa7097f5a8e92f335
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989457B2

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