(4-Chlorophenyl)hydrazine → HCID 178435590, compound

HRID 649590Notes

Reaction equation

HRID 649590 reaction equation
Cl[C:2]1[C:11]2[CH2:10][CH:9]([CH2:12][CH3:13])[CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:14]([O:16]CC)=O.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][NH2:27])=[CH:22][CH:21]=1>C(O)CCC.[OH-].[Na+]>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:14](=[O:16])[C:3]3=[CH:4][NH:5][C:6]4[CH2:7][CH2:8][CH:9]([CH2:12][CH3:13])[CH2:10][C:11]=4[C:2]3=[N:27]2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 14153005HCID 14153005, compound

Product 1

HCID 178435590HCID 178435590, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2.6 g of ethyl 4-chloro-6-ethyl-5,6,7,8-tetrahydroquinoline-3-carboxylate in 30 ml n-butanol is treated with 1.38 g of 4-chlorophenylhydrazine at room temperature under nitrogen. After stirring at room temperature overnight, the reaction mixture is heated at reflux for 41/2 hours. The reaction mixture is cooled to room temperature, the precipitate is filtered off, washed with hexane and air-dried to yield a yellow solid. The crude product is dissolved in 30 ml 1N NaOH and extracted with ether. The aqueous layer is then treated with 1.6 g of NH4Cl. The precipitate which forms is filtered off, washed with water, and dried in a vacuum oven at 120° overnight to yield 2,3,6,7,8,9-hexahydro-2-p-chlorophenyl-8-ethylpyrazolo[4,3-c]quinolin-3-(5H)-one, m.p. 318°-320°.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 41/2 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationthe precipitate is filtered off
  5. washwashed with hexane
  6. customair-dried
  7. customto yield a yellow solid
  8. extractionextracted with ether
  9. additionThe aqueous layer is then treated with 1.6 g of NH4Cl
  10. filtrationThe precipitate which forms is filtered off
  11. washwashed with water
  12. customdried in a vacuum oven at 120° overnight

Sources & evidence

ORD record
ord-8d0281216eff4d40bcd5e111528fa8aa
Source dataset
uspto-grants-1988_04
Patent number
US04740512

Reaction notes

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