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

HRID 981160노트

반응식

HRID 981160 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매4회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2676f4dd3cb44159a85837ef1dfa408a
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04990507

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