Ethyl 4-Chloroquinoline-3-carboxylate → HCID 178515192, compound

HRID 1248448Notes

Reaction equation

HRID 1248448 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[N:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[NH2:18]>C(O)C>[N:20]1[CH:21]=[CH:22][CH:23]=[N: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

4

Reactant 2

HCID 268963Ethyl 4-Chloroquinoline-3-carboxylateHCID 3465582-Hydrazinylpyrimidine

Product 1

HCID 178515192HCID 178515192, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.36 g of ethyl 4-chloroquinoline-3-carboxylate and 1.46 g of 2-hydrazinopyrimidine in 80 ml of ethanol is refluxed for 2 hours and 30 minutes. The resulting slurry is cooled down to 5°, then filtered and the resulting product is taken up in 20 ml of N sodium hydroxide and sufficient water to effect solution. Ammonium chloride (10 g) is added, the resulting precipitate is collected, and is washed three times with ethanol and three times with ether to yield 2-(2-pyrimidyl)-pyrazolo[4,3-c]quinolin-3(5H)-one, m.p. above 360°; IR (KBr) 800, 817, 844, 886 cm-1.

Workup

  1. temperatureThe resulting slurry is cooled down to 5°
  2. filtrationfiltered
  3. additionAmmonium chloride (10 g) is added
  4. customthe resulting precipitate is collected
  5. washis washed three times with ethanol and three times with ether

Sources & evidence

ORD record
ord-5ceedeb1bfd947e681848c2af255eca3
Source dataset
uspto-grants-1985_06
Patent number
US04524146

Reaction notes

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