Hydrazine → HCID 178514317, compound

HRID 1700142Notes

Reaction equation

HRID 1700142 reaction equation
[C:1]1(=O)[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[NH:3][C:2]1=[O:14])[N:10]=[CH:9][CH:8]=[CH:7]3.[NH2:16][NH2:17]>CN(C=O)C.C(O)C>[N:16](=[C:1]1[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[NH:3][C:2]1=[O:14])[N:10]=[CH:9][CH:8]=[CH:7]3)[NH2:17]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 213070621H-Pyrrolo[3,2-f]quinoline-1,2(3H)-dione

Product 1

HCID 178514317HCID 178514317, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2.3 g (12 mmol) of 3-H-pyrrolo[3,2-f]quinoline-1,2-dione (prepared from 6-aminoquinoline according to Procedure A) and 2.0 ml (0.06 mol) of hydrazine in 50 ml of DMF and 50 ml of ethanol was stirred at reflux for 2 h. The resulting suspension was allowed to cool to ambient temperature and was then chilled in an ice bath and filtered. The solid was washed with a small volume of ethanol and allowed to air dry to give 1-hydrazono-1,3-dihydropyrrolo[3,2-f]quinolin-2-one as an orange solid (1.8 g, 73%):

Workup

  1. temperatureat reflux for 2 h
  2. temperaturewas then chilled in an ice bath
  3. filtrationfiltered
  4. washThe solid was washed with a small volume of ethanol
  5. customto air dry

Sources & evidence

ORD record
ord-ef2c2aa367df4422a5b0096eeb2a48e1
Source dataset
uspto-grants-2002_02
Patent number
US06350747B1

Reaction notes

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