(4-Methoxyphenyl)hydrazine → HCID 178492062, compound

HRID 1761526Notes

Reaction equation

HRID 1761526 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][CH2:19][CH2:20][C:3]=12.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH2:30])=[CH:25][CH:24]=1>CN1CCCC1=O.O>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[C:8](=[O:10])[C:7]3[C:2]([C:3]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:4]=4[NH:5][CH:6]=3)=[N:30]2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 77023(4-Methoxyphenyl)hydrazineHCID 21241716HCID 21241716, compound

Product 1

HCID 178492062HCID 178492062, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2.00 g of ethyl 4-chloro-5,6,7,8,9,10,11,12-octahydrocyclodeca[b]pyridine-3-carboxylate and 1.12 g of 4-methoxyphenylhydrazine are stirred for eight hours in 20 ml of N-methylpyrrolidinone at 105°. The solution is then diluted with 50 ml of water and twice extracted with ether. The combined ether fractions are extracted twice with 20 ml of 1 N NaOH and the combined alkaline fractions are back-extracted with ether. The alkaline aqueous solution is then treated with an aqueous solution of 2.14 g of ammonium chloride, stirred until a solid forms; the precipitate is filtered off and dried to give 2-(4-methoxyphenyl)-2,3,6,7,8,9,10,11,12,13-decahydrocyclodeca[b]pyrazolo[3,4-d]pyridin-3(5H)-one, m.p. 143°-150°, the compound of example 5/ g.

Workup

  1. extractiontwice extracted with ether
  2. extractionThe combined ether fractions are extracted twice with 20 ml of 1 N NaOH
  3. extractionthe combined alkaline fractions are back-extracted with ether
  4. additionThe alkaline aqueous solution is then treated with an aqueous solution of 2.14 g of ammonium chloride
  5. filtrationthe precipitate is filtered off
  6. customdried

Sources & evidence

ORD record
ord-bea5036afc65412fb0f1ed7ff8fb4094
Source dataset
uspto-grants-1989_05
Patent number
US04826854

Reaction notes

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