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

HRID 889322ノート

反応式

HRID 889322 の反応式
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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-58f9ce90e92141b2b631efa48ae62d99
出典データセット
uspto-grants-2012_08
特許番号
US08252818B2

反応ノート

読み込み中…