(4-Chlorophenyl)hydrazine → HCID 178515177, compound

HRID 1194532Notes

Reaction equation

HRID 1194532 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]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16][C:15]=2[N:14]=[CH:13][C:12]=1[C:27](OCC)=[O:28]>C(O)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:27](=[O:28])[C:12]3=[CH:13][NH:14][C:15]4[CH2:16][CH2:17][CH:18]([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[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 13713230HCID 13713230, compound

Product 1

HCID 178515177HCID 178515177, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1.2 g of p-chlorophenylhydrazine and 2.25 g of ethyl 4-chloro-6-phenyl-5,6,7,8-tetrahydroquinoline-3-carboxylate (Example 1e) in 100 mL of n-butanol is refluxed overnight, then evaporated to dryness. The residue is triturated with ether and filtered. Collected solid is dissolved in ethanol, decolorized with charcoal, concentrated to a smaller volume and cooled to deposit a solid, which is recrystallized from ethanol to yield 2-p-chlorophenyl-2,3,6,7,8,9-hexahydro-8-phenylpyrazolo[4,3-c]-quinolin-3(5H)-one, m.p. 333°-335°.

Workup

  1. temperatureis refluxed overnight
  2. customevaporated to dryness
  3. customThe residue is triturated with ether
  4. filtrationfiltered
  5. customCollected solid
  6. dissolutionis dissolved in ethanol
  7. concentrationconcentrated to a smaller volume
  8. temperaturecooled
  9. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-bb45652d7ad2424dbac4a17dc4069b2b
Source dataset
uspto-grants-1989_03
Patent number
US04814450

Reaction notes

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