(4-Chlorophenyl)hydrazine → HCID 178423471, compound

HRID 745950Notes

Reaction equation

HRID 745950 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][CH:18]([CH3:21])[CH2:17][CH2:16][C:15]=2[N:14]=[CH:13][C:12]=1[C:22](OCC)=[O:23]>C1(C)C(C)=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:22](=[O:23])[C:12]3=[CH:13][NH:14][C:15]4[CH2:16][CH2:17][CH:18]([CH3:21])[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 13713231HCID 13713231, compound

Product 1

HCID 178423471HCID 178423471, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 1.37 g of p-chlorophenylhydrazine and 2.4 g of ethyl 4-chloro-6-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate in 75 mL of xylene is stirred and refluxed overnight, then cooled to room temperature and filtered. Collected solid is dissolved in hot ethanol, treated with decolorizing charcoal, and concentrated to a smaller volume to deposit a solid, which is recrystallized from ethanol containing hydrogen chloride to yield 2-p-chlorophenyl-2,3,6,7,8,9-hexahydro-8-methylpyrazolo[4,3-c]quinolin-3(5H)-one hydrochloride, m.p. 331°-333°.

Workup

  1. temperaturerefluxed overnight
  2. filtrationfiltered
  3. customCollected solid
  4. dissolutionis dissolved in hot ethanol
  5. additiontreated with decolorizing charcoal
  6. concentrationconcentrated to a smaller volume
  7. customis recrystallized from ethanol
  8. additioncontaining hydrogen chloride

Sources & evidence

ORD record
ord-0b219f1bde2b4c76ba3d5ecfd0e09fbf
Source dataset
uspto-grants-1986_07
Patent number
US04602014

Reaction notes

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