(4-Chlorophenyl)hydrazine → HCID 178423471, compound

HRID 649577Notes

Reaction equation

HRID 649577 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-408e98fdb2da485f9535588b74467610
Source dataset
uspto-grants-1988_04
Patent number
US04740512

Reaction notes

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