1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 178515188, compound

HRID 1106252Notes

Reaction equation

HRID 1106252 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:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[NH2:18].C1(OC2C=CC=CC=2)C=CC=CC=1.C1(C2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[N:17]1[C:12](=[O:14])[C:3]2=[CH:4][NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]2=[N:18]1

Participants

5

Reactant 3

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 786452-HydrazinopyridineHCID 268963Ethyl 4-Chloroquinoline-3-carboxylate

Product 1

HCID 178515188HCID 178515188, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The mixture of 4.0 g of ethyl 4-chloroquinolin-3-carboxylate, 2.04 g of 2-hydrazinopyridine and 50 ml of eutectic diphenyl ether-biphenyl is stirred at 110°-130° for 3 hours under nitrogen. After cooling to room temperature it is diluted with diethyl ether, filtered, the solids washed with diethyl ether and dissolved in 100 ml of aqueous sodium hydroxide. The solution is washed with diethyl ether and the pH thereof adjusted to 8.5 by addition of ammonium chloride. The precipitate formed is collected, washed successively with water, methanol and diethyl ether, to yield the 2-(2-pyridyl)-pyrazolo[4,3-c]quinolin-3(5H)-one showing in the IR-spectrum peaks at 887, 865, 853, 788, 780, 765, 756, 737 and 726 cm-1.

Workup

  1. filtrationfiltered
  2. washthe solids washed with diethyl ether
  3. dissolutiondissolved in 100 ml of aqueous sodium hydroxide
  4. washThe solution is washed with diethyl ether
  5. additionthe pH thereof adjusted to 8.5 by addition of ammonium chloride
  6. customThe precipitate formed
  7. customis collected
  8. washwashed successively with water, methanol and diethyl ether

Sources & evidence

ORD record
ord-fe32bc93177946d68a24f1a0132cafac
Source dataset
uspto-grants-1982_01
Patent number
US04312870

Reaction notes

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