Pyridine → N-(5-chloropyridin-2-yl)-5-methyl-2-nitrobenzamide

HRID 514718

反応式

HRID 514718 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=1.N1C=CC=CC=1>ClCCl.CN(C)C=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:7]([C:6]2[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])=[O:9])=[N:22][CH:23]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 183715-Methyl-2-nitrobenzoic acidHCID 65578Oxalyl chlorideHCID 661742-Amino-5-chloropyridine

生成物 1

HCID 3562519N-(5-chloropyridin-2-yl)-5-methyl-2-nitrobenzamide収率 92%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-methyl-2-nitrobenzoic acid (1 g, 5.52 mmol) in dichloromethane (5 ml) was added oxalyl chloride (0.964 ml, 11.04 mmol) and a few drops of dimethylformamide. The mixture was stirred at r.t. for 2 hrs. After the evaporation of the solvent, the residue was dissolved in dichloromethane (5 ml). 2-amino-5-chloropyridine (852 mg, 6.62 mmol) and pyridine (1.34 ml, 16.56 mmol) were added to the solution. The mixture was stirred at r.t. overnight. After the evaporation of the solvent, the crude residue was purified by silica gel column chromatography using solvent system 25% ethyl acetate in hexane as eluent to give N-(5-chloro(2-pyridyl))(5-methyl-2-nitrophenyl)carboxamide as a solid (1.48 g, 92%). MS found for C13H10ClN3O3 M+=291, (M+2)+=293.

後処理

  1. customAfter the evaporation of the solvent
  2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  3. stirringThe mixture was stirred at r.t. overnight
  4. customAfter the evaporation of the solvent
  5. customthe crude residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-93b26794861d47f1a0e6ebccb94af737
出典データセット
uspto-grants-2015_08
特許番号
US09108922B2

関連ノート

読み込み中…