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

HRID 2106827Notes

Reaction equation

HRID 2106827 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of ethyl 2-bromomethyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (1.5 g) and 2-dimethylaminoethylamine (0.6 g) is 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).

Workup

  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

Sources & evidence

ORD record
ord-3ac14c789df84ebdb5120733f721ff65
Source dataset
uspto-grants-1990_06
Patent number
US04931453

Reaction notes

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