(4-Chlorophenyl)hydrazine → HCID 178423471, compound

HRID 1194533Notes

Reaction equation

HRID 1194533 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-40312daa6d5341d48cccf982033b021b
Source dataset
uspto-grants-1989_03
Patent number
US04814450

Reaction notes

Loading…