2-Hydrazinoethanol → 6-[2-(2-Hydroxyethyl)-5-methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl]-1-methyl-1,2,3,4-tetrahydroquinolin-2-one

HRID 128014

Reaction equation

HRID 128014 reaction equation
O=[C:2]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[C:14](=[O:20])[CH2:13][CH2:12]2)[CH:3]([CH3:8])[CH2:4][C:5]([OH:7])=O.[NH:21]([CH2:23][CH2:24][OH:25])[NH2:22]>C(O)C>[OH:25][CH2:24][CH2:23][N:21]1[C:5](=[O:7])[CH2:4][CH:3]([CH3:8])[C:2]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14](=[O:20])[CH2:13][CH2:12]3)=[N:22]1

Participants

4

Reactant 2

HCID 80172-HydrazinoethanolHCID 155745774-Oxo-4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-3-methylbutanoic acid

Product 1

HCID 234715436-[2-(2-Hydroxyethyl)-5-methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl]-1-methyl-1,2,3,4-tetrahydroquinolin-2-oneYield 80.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.72 g of 4-oxo-4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-3-methylbutanoic acid and 1.5 g of 2-hydrazinoethanol in 30 ml of ethanol was heated under reflux on a water bath for 2 hours. The reaction mixture was concentrated under reduced pressure and water was added to the residue. The precipitated crystals were filtered off and recrystallized from isopropanol to give 2.5 g of 6-[2-(2-hydroxyethyl)-5-methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl]-1-methyl-1,2,3,4-tetrahydroquinolin-2-one as colorless crystals, melting at 171°-173° C.

Workup

  1. temperatureunder reflux on a water bath for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure and water
  3. additionwas added to the residue
  4. filtrationThe precipitated crystals were filtered off
  5. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-7e0bac69001e4998af08aa82ba068df7
Source dataset
uspto-grants-1981_03
Patent number
US04258185

Linked notes

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