1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 178515187, compound

HRID 1106249Notes

Reaction equation

HRID 1106249 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[C:21]([O:23]CC)=O.C1(OC2C=CC=CC=2)C=CC=CC=1.C1(C2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:21](=[O:23])[C:12]2=[CH:13][NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:11]2=[N:10]1

Participants

4

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 12909446HCID 12909446, compound

Product 1

HCID 178515187HCID 178515187, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The mixture of 3.5 g of ethyl 4-(2,4-dichlorophenyl-hydrazino)-quinolin-3-carboxylate and 40 ml of eutectic diphenyl ether-biphenyl is heated to 175° for 4 hours, cooled to room temperature and diluted with diethyl ether. The resulting suspension is filtered, the residue washed with diethyl ether and dissolved in N aqueous sodium hydroxide. The solution is washed with diethyl ether, its pH adjusted to 8.5 with ammonium chloride and the precipitate formed collected. It is washed successively with hot water, methanol and diethyl ether, to yield the 2-(2,4-dichlorophenyl)-pyrazolo[4,3-c]-quinolin-3(5H)-one, showing peaks in the IR-spectrum at 890, 867, 845, 832, 816, 796, 775, 767, 756, 730 and 701 cm-1.

Workup

  1. temperatureis heated to 175° for 4 hours
  2. filtrationThe resulting suspension is filtered
  3. washthe residue washed with diethyl ether
  4. dissolutiondissolved in N aqueous sodium hydroxide
  5. washThe solution is washed with diethyl ether, its pH
  6. customthe precipitate formed
  7. customcollected
  8. washIt is washed successively with hot water, methanol and diethyl ether

Sources & evidence

ORD record
ord-dd575dcc38634078b6c0dc4322aa4cde
Source dataset
uspto-grants-1982_01
Patent number
US04312870

Reaction notes

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