Hydroxyamine hydrochloride → 6,7-dihydro-8(5H)-quinolinone oxime

HRID 1452029Notes

Reaction equation

HRID 1452029 reaction equation
O=[C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.Cl.[NH2:13][OH:14].C([O-])(=O)C.[Na+]>C(O)C.O.O>[N:13](=[C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1)[OH:14]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 117447776,7-Dihydro-5H-quinoline-8-one

Product 1

HCID 1357421856,7-dihydro-8(5H)-quinolinone oximeYield 79.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

A solution of 2.22 g of 8-oxo-5,6,7,8-tetrahydroquinoline, 2.1 g of hydroxylamine hydrochloride, and 4.1 g of sodium acetate in 15 mL of 3:1 ethanol-water was heated at 70° C. for 1 h. The reaction mixture was then diluted with water and extracted with dichloromethane. Evaporation of the extracts gave 1.95 g of product which was pure enough by NMR to be used in the next step.

Workup

  1. extractionextracted with dichloromethane
  2. customEvaporation of the extracts

Sources & evidence

ORD record
ord-616f9980b82548c1bbd84bb66d83f319
Source dataset
uspto-grants-1997_02
Patent number
US05606054

Reaction notes

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