Water → HCID 178510016, compound

HRID 1106258Notes

Reaction equation

HRID 1106258 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.[C:17]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][NH2:26])=[CH:21][CH:20]=1)#[N:18].[OH-].[Na+].O>C1(C)C(C)=CC=CC=1>[C:17]([C:19]1[CH:24]=[CH:23][C:22]([N:25]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:26]2)=[CH:21][CH:20]=1)#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 268963Ethyl 4-Chloroquinoline-3-carboxylateHCID 5837844-Hydrazinobenzonitrile

Product 1

HCID 178510016HCID 178510016, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

38.5 ml of a 0.17 M solution of ethyl 4-chloroquinoline-3-carboxylate in xylene, and 0.96 g of p-cyanophenylhydrazine in 30 ml of xylene are mixed and heated at 115° to 120° for 3 hours. The mixture is then cooled to room temperature, and stirred with 20 ml of 1 N aqueous sodium hydroxide and sufficient water to dissolve all solids. The aqueous layer is separated, washed twice with diethyl ether, then treated with an aqueous solution of 1.07 g ammonium chloride, and the resulting precipitate is collected, washed with water and dried to yield the 2-(p-cyanophenyl)-pyrazolo[4,3-c]quinolin-3(5H)-one, showing peaks in the IR-spectrum at 885, 830, 780, 755 and 730 cm-1.

Workup

  1. temperatureheated at 115° to 120° for 3 hours
  2. dissolutionto dissolve all solids
  3. customThe aqueous layer is separated
  4. washwashed twice with diethyl ether
  5. additiontreated with an aqueous solution of 1.07 g ammonium chloride
  6. customthe resulting precipitate is collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-84c550626ae847d5b32d950015eebc2e
Source dataset
uspto-grants-1982_01
Patent number
US04312870

Reaction notes

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