Methylamine → 2-Chloro-N-methylnicotinamide

HRID 1986101노트

반응식

HRID 1986101 반응식
CN.[CH2:3]([N:5](CC)CC)C.[Cl:10][C:11]1[N:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14]>CC#N>[Cl:10][C:11]1[N:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH:5][CH3:3])=[O:14]

참가 물질

5

반응물 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 27745412-Chloronicotinoyl chloride

생성물 1

HCID 122869552-Chloro-N-methylnicotinamide수율 31.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
23 °C

실험 절차

Methanamine (0.425 mL, 3.41 mmol) and triethylamine (0.792 mL, 5.68 mmol) were dissolved in CH3CN (14.2 mL) at 23° C. 2-Chloronicotinoyl chloride (500 mg, 2.84 mmol) was added and the reaction mixture was stirred at 23° C. for 16 h. The solvent was removed by rotary evaporation and the residue was partitioned between EtOAc (20 mL) and sat. aq. NaHCO3 (20 mL). The aqueous phase was extracted with EtOAc (3×20 mL). The combined organic phases were dried over MgSO4 and concentrated. Trituration of the resulting solid with 5% EtOAc-hexane provided the desired product as a white powder (153.2 mg, 31%). 1H NMR (CD3OD) δ 8.43 (dd, 1H, J=5.09, 2.03 Hz), 7.88 (dd, 1H, J=7.63, 2.03 Hz), 7.45 (dd, 1H, J=7.38, 4.83 Hz), 2.91 (s, 3H); MS(ESI+) m/z 171.1 (M+H)+.

후처리

  1. customThe solvent was removed by rotary evaporation
  2. customthe residue was partitioned between EtOAc (20 mL) and sat. aq. NaHCO3 (20 mL)
  3. extractionThe aqueous phase was extracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-de6be18994c24b7dbd2305fa1e3f484a
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547782B2

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