N,N-Dimethylethylenediamine → 6-(2-dimethylaminoethyl)-4-(3-nitrophenyl)-5-oxo-2-phenyl-5,7-dihydro-(6H)-pyrrolo[3,4-b]pyridine

HRID 1762164ノート

反応式

HRID 1762164 の反応式
Br[CH2:2][C:3]1[C:8]([C:9]([O:11]CC)=O)=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[CH:6]=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:4]=1.[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][NH2:33]>C(O)(C)C>[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][N:33]1[C:9](=[O:11])[C:8]2[C:3](=[N:4][C:5]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:6][C:7]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[CH2:2]1

参加物

4

反応物 2

HCID 66053N,N-DimethylethylenediamineHCID 10388561Ethyl 2-bromomethyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate

生成物 1

HCID 103637436-(2-dimethylaminoethyl)-4-(3-nitrophenyl)-5-oxo-2-phenyl-5,7-dihydro-(6H)-pyrrolo[3,4-b]pyridine収率 35.8%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A mixture of ethyl 2-bromomethyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (1.5 g) and 2-dimethylaminoethylamine (0.6 g) in isopropyl alcohol (15 ml) was refluxed for 1 hour. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of water (20 ml) and chloroform (40 ml). The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off. The residue was subjected to a column chromatography on silica gel, eluting with a mixture of chloroform and methanol (50:1 V/V). The fractions containing the desired compound were combined and evaporated in vacuo. The crystalline residue was recrystallized from ethanol to give 6-(2-dimethylaminoethyl)-4-(3-nitrophenyl)-5-oxo-2-phenyl-5,7-dihydro-(6H)-pyrrolo[3,4-b]pyridine (0.49 g).

後処理

  1. temperaturewas refluxed for 1 hour
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in a mixture of water (20 ml) and chloroform (40 ml)
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. washeluting with a mixture of chloroform and methanol (50:1 V/V)
  8. additionThe fractions containing the desired compound
  9. customevaporated in vacuo
  10. customThe crystalline residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-84b5402af2df4720b1a735b2081bad88
出典データセット
uspto-grants-1989_05
特許番号
US04831030

反応ノート

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