Methylamine → 2-Chloro-N-methylnicotinamide

HRID 1986101ノート

反応式

HRID 1986101 の反応式
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]

参加物

5

反応物 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 27745412-Chloronicotinoyl chloride

生成物 1

HCID 122869552-Chloro-N-methylnicotinamide収率 31.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
23 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-de6be18994c24b7dbd2305fa1e3f484a
出典データセット
uspto-grants-2009_06
特許番号
US07547782B2

反応ノート

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