Sodium Hydroxide → HCID 178492060, compound

HRID 1905682Notes

Reaction equation

HRID 1905682 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-6826df919c8a4e99a2b73a20ca82c1be
Source dataset
uspto-grants-1987_03
Patent number
US04647566

Reaction notes

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