Sodium Hydroxide → HCID 178492060, compound

HRID 745951Notes

Reaction equation

HRID 745951 reaction equation
Cl[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:12]([O:14]CC)=O.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][NH2:26])=[CH:21][CH:20]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:12](=[O:14])[C:3]3=[CH:4][NH:5][C:6]4[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=4[C:2]3=[N:26]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 77023(4-Methoxyphenyl)hydrazineHCID 13713229Ethyl 4-chloro-5,6,7,8-tetrahydro-3-quinolinecarboxylate

Product 1

HCID 178492060HCID 178492060, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.44 g of ethyl 4-chloro-5,6,7,8-tetrahydroquinoline-3-carboxylate and 3.45 g of 4-methoxyphenylhydrazine is refluxed 18 hrs in 100 ml toluene. The resulting mixture is stirred with 50 ml 1N NaOH, the layers separated, and the aqueous phase extracted twice with ether. The aqueous layer is then neutralized with aqueous ammonium chloride and filtered. The product is washed with water, and dried to give 2-(4-methoxyphenyl)-2,3,6,7,8,9-hexahydropyrazolo[4,3-c]quinolin-3(5H)-one m.p. 279°-282°.

Workup

  1. customthe layers separated
  2. extractionthe aqueous phase extracted twice with ether
  3. filtrationfiltered
  4. washThe product is washed with water
  5. customdried

Sources & evidence

ORD record
ord-0386571fd98449948f8d02ccf3ea7b41
Source dataset
uspto-grants-1986_07
Patent number
US04602014

Reaction notes

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