4-Aminopyridine → 4-methoxy-N-(pyridin-4-yl)benzamide

HRID 33936

반응식

HRID 33936 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:8](Cl)(=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]([NH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[O:17])=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 17274-AminopyridineHCID 7477p-Anisoyl chlorideHCID 8471Triethylamine

생성물 1

HCID 6676114-methoxy-N-(pyridin-4-yl)benzamide수율 81%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-Aminopyridine (1.94 g, 20.6 mmol) was added to a solution of p-anisoyl chloride (3.5 g, 20.6 mmol) and triethylamine (8.6 mL, 62 mmol) in dichloromethane (100 mL) at 0° C. The mixture was stirred 3 h at RT, and then extracted successively with 1N NaOH, water and brine, dried over sodium sulfate, and concentrated. Chromatography on silica (gradient of 30% to 100% ethyl acetate-hexanes) gave 3.8 g (81%) of a colorless solid. 1H NMR (CDCl3, 400 mHz) δ 8.49 (m, 2H), 8.19 (br, 1H), 7.85 (m, 2H), 7.59 (m, 2H), 6.95 (m, 2H), 3.85 (s, 3H), MS (AP+) 229 (MH+).

후처리

  1. extractionextracted successively with 1N NaOH, water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2dd297b8f19a47c494c6cf1b046d20b0
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429665B2

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