(4-Methoxyphenyl)hydrazine → HCID 178492061, compound

HRID 1761520Notes

Reaction equation

HRID 1761520 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:3]=12.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][NH2:28])=[CH:23][CH:22]=1>C(O)CCC>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[C:8](=[O:10])[C:7]3[C:2]([C:3]4[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:4]=4[NH:5][CH:6]=3)=[N:28]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 77023(4-Methoxyphenyl)hydrazineHCID 14500574HCID 14500574, compound

Product 1

HCID 178492061HCID 178492061, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2.24 g of ethyl 4-chloro-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carboxylate and 1.16 g of 4-methoxyphenylhydrazine is stirred and heated at reflux under a nitrogen atmosphere for 20 hours in 20 ml of n-butanol. The solvent is then evaporated under reduced pressure and the residual material stirred with 20 ml of 1N sodium hydroxide, ether, and water. The layers are separated, the aqueous phase is extracted with ether and then treated with an aqueous solution of 1.07 g of ammonium chloride. The precipitate is filtered off and washed with water to give 2-(4-methoxyphenyl)-2,3,6,7,8,9,10,11-octahydrocycloocta[b]pyrazolo[3,4-d]pyridin-3(5H)-one, m.p. 275°-277°, the compound of formula II wherein n represents the integer 6, R4 and R5 represent hydrogen, and R1 represents p-methoxyphenyl. Further purification gives m.p. 283°-285°.

Workup

  1. temperatureheated
  2. customThe solvent is then evaporated under reduced pressure
  3. stirringthe residual material stirred with 20 ml of 1N sodium hydroxide, ether, and water
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted with ether
  6. additiontreated with an aqueous solution of 1.07 g of ammonium chloride
  7. filtrationThe precipitate is filtered off
  8. washwashed with water

Sources & evidence

ORD record
ord-cd9a53060dad48ef86cc7c2eada0b10a
Source dataset
uspto-grants-1989_05
Patent number
US04826854

Reaction notes

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