Ethanol → HCID 23471607, compound

HRID 128020Notes

Reaction equation

HRID 128020 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([CH:14]3OC(=O)[CH2:16][CH2:15]3)=O)=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:20].[OH2:21].[NH2:22][NH2:23].[CH2:24]([OH:26])C>>[OH:26][CH2:24][CH:14]1[C:12]([C:8]2[CH2:7][CH:6]3[C:11](=[CH:10][CH:9]=2)[N:2]([CH3:1])[C:3](=[O:20])[CH2:4][CH2:5]3)=[N:23][NH:22][C:16](=[O:21])[CH2:15]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 23471609HCID 23471609, compound

Product 1

HCID 23471607HCID 23471607, compound

Procedure

A solution of 4.9 g of 4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)carbonyl-γ-butyrolactone and 3.0 ml of 85% hydrazine hydrate in 50 ml of ethanol was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure and ice-cold water was added to the residue. After the mixture was allowed to stand, the precipitated crystals were filtered off and recrystallized from water to give 2.5 g of 6-(5-hydroxymethyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1-methyl-1,2,4,5-tetrahydroquinolin-2-one as colorless prisms, melting at 201°-204° C.

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure and ice-cold water
  3. additionwas added to the residue
  4. filtrationthe precipitated crystals were filtered off
  5. customrecrystallized from water

Sources & evidence

ORD record
ord-53a5e80a7a434c06897cf1c914e17aa6
Source dataset
uspto-grants-1981_03
Patent number
US04258185

Reaction notes

Loading…