P-Anisidine → 6-chloro-N-(4-methoxyphenyl)pyridine-3-carboxamide

HRID 889322노트

반응식

HRID 889322 반응식
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].S(Cl)([Cl:28])=O>>[Cl:28][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[O:8])=[CH:4][N:3]=1

참가 물질

5

반응물 4

HCID 7732P-AnisidineHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 2389326-Bromonicotinic acid

생성물 1

HCID 14832696-chloro-N-(4-methoxyphenyl)pyridine-3-carboxamide

실험 절차

6-Bromonicotinic acid (200 mg, 0.99 mmol) was heated at reflux in thionyl chloride (2 ml) for 3 hrs. The reaction was allowed to cool to room temperature and the excess thionyl chloride evaporated under vacuum. The residue was dissolved in DCM (2 ml), p-anisidine (123 mg, 0.10 mmol) and sodium carbonate (500 mg) were added to the solution. The reaction was stirred at room temperature for 4 hrs, filtered and the filtrate reduced to dryness under vacuum to give 6-chloro-N-(4-methoxyphenyl)nicotinamide. NMR: δH [2H6]-DMSO 10.37,(1H, b), 8.94,(1H, d), 8.34,(1H, dd), 7.70,(1H, d), 7.66,(2H, m), 6.95,(2H, m), 3.75,(3H, s).

후처리

  1. customthe excess thionyl chloride evaporated under vacuum
  2. dissolutionThe residue was dissolved in DCM (2 ml)
  3. filtrationfiltered

출처 및 근거

ORD 기록
ord-58f9ce90e92141b2b631efa48ae62d99
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252818B2

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