3-Hydrazinylquinoline → HCID 178515191, compound

HRID 1248450Notes

Reaction equation

HRID 1248450 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14]CC)=O.[NH:17]([C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH2:18]>C1(C)C(C)=CC=CC=1>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[C:19]([N:17]2[C:12](=[O:14])[C:3]3=[CH:4][NH:5][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=4[C:2]3=[N:18]2)[CH:20]=1

Participants

4

Reactant 2

HCID 1091063-HydrazinylquinolineHCID 268963Ethyl 4-Chloroquinoline-3-carboxylate

Product 1

HCID 178515191HCID 178515191, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 11.8 g of ethyl 4-chloroquinoline-3-carboxylate and 8.7 g of 3-hydrazinoquinoline is refluxed for 51/2 hours in 300 ml of xylene. The reaction mixture is allowed to stand for 16 hours at 23°. The solvent is decanted from an oily solid. This solid is slurried twice in 80 ml of xylene, the solvent is decanted and the residue is stirried for 1 hour in 150 ml of IN sodium hydroxide, 150 ml of water and 220 ml of xylene. The mixture is filtered, the aqueous layer is separated and 12 g of ammonium chloride is added while stirring. The resulting slurry is heated on the steam bath for one hour, allowed to cool down to 30° and then filtered. The solid is washed three times with water, twice with ether-acetone (2:1) and twice with ether. Recrystallization from dimethylformamide gives 2-(3-quinolyl)pyrazolo[4,3-c]quinolin-3(5H)-one, m.p. above 350°; IR (KBr) 802, 852, 858, 882, 895 cm-1.

Workup

  1. customThe solvent is decanted from an oily solid
  2. customthe solvent is decanted
  3. waitthe residue is stirried for 1 hour in 150 ml of IN sodium hydroxide, 150 ml of water and 220 ml of xylene
  4. filtrationThe mixture is filtered
  5. customthe aqueous layer is separated
  6. addition12 g of ammonium chloride is added
  7. temperatureThe resulting slurry is heated on the steam bath for one hour
  8. temperatureto cool down to 30°
  9. filtrationfiltered
  10. washThe solid is washed three times with water
  11. customRecrystallization from dimethylformamide

Sources & evidence

ORD record
ord-e3a86e8050684cf58fc9dd07804a18f5
Source dataset
uspto-grants-1985_06
Patent number
US04524146

Reaction notes

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