O-Xylene → HCID 178433617, compound

HRID 1106250Notes

Reaction equation

HRID 1106250 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[C:3]=1[C:13]([O:15]CC)=O.[C:18]1([NH:24][NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(C)C(C)=CC=CC=1>C(OCC)C>[CH3:12][C:4]1[NH:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[C:2]2[C:3]=1[C:13](=[O:15])[N:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[N:25]=2

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 7516PhenylhydrazineHCID 105386043-Quinolinecarboxylic acid, 4-chloro-2-methyl-, ethyl ester

Product 1

HCID 178433617HCID 178433617, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The mixture of 3.6 g of ethyl 4-chloro-2-methylquinolin-3-carboxylate, 1.8 g of phenylhydrazine and 40 ml of xylene is refluxed for 4 hours, cooled to room temperature, diluted with diethyl ether and filtered. The residue is dissolved in 50 ml of 2 N aqueous sodium hydroxide, the solution washed with diethyl ether and its pH adjusted to 8.5 with ammonium chloride. The precipitate formed is collected, washed successively with hot water, methanol and diethyl ether, to yield the 4-methyl-2-phenylpyrazolo[4,3-c]quinolin-3(5H)-one, showing in the IR-spectrum peaks at 874, 867, 858, 850, 822, 780, 765, 756, 750, 740 and 722 cm-1. Analogously the 4-methyl-2-(p-chlorophenyl)-pyrazolo[4-3,-c]quinolin-3(5H)-one is prepared, melting at 349°-350°.

Workup

  1. temperatureis refluxed for 4 hours
  2. filtrationfiltered
  3. dissolutionThe residue is dissolved in 50 ml of 2 N aqueous sodium hydroxide
  4. washthe solution washed with diethyl ether and its pH
  5. customThe precipitate formed
  6. customis collected
  7. washwashed successively with hot water, methanol and diethyl ether

Sources & evidence

ORD record
ord-7b46845f285841a28ed0369a24ca0a90
Source dataset
uspto-grants-1982_01
Patent number
US04312870

Reaction notes

Loading…