2-Amino-5-methylbenzonitrile → 6-Chloro-N-(2-cyano-4-methylphenyl)-3-pyridinecarboxamide

HRID 1007229노트

반응식

HRID 1007229 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[C:4]#[N:5].[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][N:13]=1>N1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[Cl:11][C:12]1[N:13]=[CH:14][C:15]([C:16]([NH:1][C:2]2[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=2[C:4]#[N:5])=[O:17])=[CH:19][CH:20]=1

참가 물질

5

반응물 2

HCID 2427782-Amino-5-methylbenzonitrileHCID 27821656-Chloronicotinoyl Chloride

생성물 1

HCID 98351946-Chloro-N-(2-cyano-4-methylphenyl)-3-pyridinecarboxamide수율 18.1%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 21226206Ethyl acetate hexane용매

실험 절차

A mixture of 2-amino-5-methyl-benzonitrile (80 mg, 0.61 mmol) and 6-chloronicotinoyl chloride (162 mg, 0.92 mmol) in anhydrous pyridine (5 ml) was refluxed for 4 hours. The mixture was diluted with 50 ml of hexane:ethyl acetate (1:1), wash with 2 N HCl (25 ml), water (25 ml), followed by saturated aqueous NaCl (25 ml), dried over anhydrous sodium sulfate, and evaporated. The crude product was purified by column chromatography using hexane:ethyl acetate (2:1) to give 30 mg (18% yield) of the title compound as pale pink solid. 1H NMR (DMSO-d6): 10.82 (s, 1H), 8.99 (d, J=2.4 Hz, 1H), 8.38 (dd, J=2.4, 8.1 Hz, 1H), 7.78-7.73 (m, 2H), 7.61-7.48 (m, 2H), 2.38 (s, 3H).

후처리

  1. temperaturewas refluxed for 4 hours
  2. washwash with 2 N HCl (25 ml), water (25 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-53fda81b15f743b49c274daa63d91126
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794397B2

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