Sodium Hydroxide → 3-(2-Dimethylaminoethylcarbamoyl)-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine

HRID 981160ノート

反応式

HRID 981160 の反応式
[CH3:1][C:2]1[C:7]([C:8](O)=[O:9])=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:5]=[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1.S(Cl)(Cl)=O.[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH2:34].[OH-].[Na+]>C(Cl)Cl.O.CN(C)C=O>[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH:34][C:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:5][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)=[O:9]

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 66053N,N-DimethylethylenediamineHCID 104720472-Methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid

生成物 1

HCID 104089363-(2-Dimethylaminoethylcarbamoyl)-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine収率 36.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒4 回

実験手順

To a mixture of 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid (1.98 g), methylene chloride (20 ml) and N,N-dimethylformamide (4 ml) was added a solution of thionyl chloride (0.47 ml) in methylene chloride (2 ml) at 7° C. under ice cooling. After stirring for 2.5 hours at the same condition, a solution of 2-dimethylaminoethylamine (1.3 g), in methylene chloride (20 ml) was added thereto and stirred for 2 hours at the same temperature. After adding water 9150 ml) and methylene chloride (150 ml) thereto, the mixture was adjusted to pH 9.0 with 10% aqueous sodium hydroxide. The organic layer was separated, washed successively with water and saturated brine, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a column chromatography on alumina (70 g) and eluted with chloroform. The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was recrystallized from diethyl ether to give 3-(2-dimethylaminoethylcarbamoyl)-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine (0.88 g).

後処理

  1. stirringstirred for 2 hours at the same temperature
  2. customThe organic layer was separated
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. washeluted with chloroform
  7. additionThe fractions containing the object compound
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from diethyl ether

出典と根拠

ORDレコード
ord-2676f4dd3cb44159a85837ef1dfa408a
出典データセット
uspto-grants-1991_02
特許番号
US04990507

反応ノート

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