(4-Chlorophenyl)hydrazine → HCID 178479603, compound

HRID 745948Notes

Reaction equation

HRID 745948 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.Cl[C:11]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[N:14]=[CH:13][C:12]=1[C:21](OCC)=[O:22]>C(O)CCC>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:21](=[O:22])[C:12]3=[CH:13][NH:14][C:15]4[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=4[C:11]3=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 13713229Ethyl 4-chloro-5,6,7,8-tetrahydro-3-quinolinecarboxylate

Product 1

HCID 178479603HCID 178479603, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3.0 g of p-chlorophenylhydrazine and 4.5 g of ethyl 4-chloro-5,6,7,8-tetrahydroquinoline-3-carboxylate (Example 2b) in 150 mL of n-butanol is refluxed for 24 hours under nitrogen atmosphere. The mixture is then evaporated to dryness and the residue is triturated with ether obtaining a yellow solid. This material is dissolved in 750 mL of hot ethanol, decolorized with charcoal, and concentrated to a smaller volume to precipitate a yellow crystalline solid. This material is recrystallized from ethanol containing hydrogen chloride. Crystals are collected, washed with ether and dried in vacuum oven at 80° overnight obtaining 2-p-chlorophenyl-2,3,6,7,8,9-hexahydropyrazolo[4,3-c]quinolin-3(5H)-one hydrochloride, m.p. 284°.

Workup

  1. temperatureis refluxed for 24 hours under nitrogen atmosphere
  2. customThe mixture is then evaporated to dryness
  3. customthe residue is triturated with ether obtaining a yellow solid
  4. dissolutionThis material is dissolved in 750 mL of hot ethanol
  5. concentrationconcentrated to a smaller volume
  6. customto precipitate a yellow crystalline solid
  7. customThis material is recrystallized from ethanol
  8. additioncontaining hydrogen chloride
  9. customCrystals are collected
  10. washwashed with ether
  11. customdried in vacuum oven at 80° overnight

Sources & evidence

ORD record
ord-c59656fd9fc94259879ec833af3da0c7
Source dataset
uspto-grants-1986_07
Patent number
US04602014

Reaction notes

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