(4-Chlorophenyl)hydrazine → HCID 178479604, compound

HRID 649579Notes

Reaction equation

HRID 649579 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:16]([C:17](OCC)=[O:18])=[CH:15][N:14]=[C:13]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:12]=12>C(O)CCC>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11]([C:12]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][C:13]=4[NH:14][CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 21270435Ethyl 4-chloro-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate

Product 1

HCID 178479604HCID 178479604, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2.6 g of p-chlorophenylhydrazine and 3.9 g of ethyl 4-chloro-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (Example 2c) in 100 mL of n-butanol is refluxed overnight under nitrogen atmosphere, then cooled to room temperature. The solid precipitate is collected, triturated with ether, dissolved in hot ethanol and decolorized with charcoal. The ethanolic solution is acidified with hydrogen chloride, then concentrated to a smaller volume and diluted with ether to precipitate a yellow solid, which is collected, washed with ether and dried at 90° in vacuum overnight, obtaining 2-p-chlorophenyl-2,3,5,6,7,8,9,10-octahydrocyclohepta[b]pyrazolo[3,4-d]pyridin-3-one hydrochloride, m.p. 272°-275°.

Workup

  1. temperatureis refluxed overnight under nitrogen atmosphere
  2. customThe solid precipitate is collected
  3. customtriturated with ether
  4. dissolutiondissolved in hot ethanol
  5. concentrationconcentrated to a smaller volume
  6. additiondiluted with ether
  7. customto precipitate a yellow solid, which
  8. customis collected
  9. washwashed with ether
  10. customdried at 90° in vacuum overnight

Sources & evidence

ORD record
ord-a5fc0a92551144c7ab2fccb852bbbce0
Source dataset
uspto-grants-1988_04
Patent number
US04740512

Reaction notes

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