Ethanol → 3-Methyl-8-oximino-5,6,7,8-tetrahydroquinoline

HRID 1730013Notes

Reaction equation

HRID 1730013 reaction equation
[NH:1]1[C:10]2C(=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=O.Cl.[NH2:13][OH:14].[OH-].[Na+].[CH2:17](O)[CH3:18]>O>[CH3:6][C:7]1[CH:8]=[N:9][C:10]2[C:1](=[N:13][OH:14])[CH2:2][CH2:3][CH2:4][C:18]=2[CH:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 60382-HydroxyquinolineHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 1362302603-Methyl-8-oximino-5,6,7,8-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The quinolinone (30g), hydroxylamine hydrochloride (14g), sodium hydroxide (9g), ethanol (165ml) and water (65ml) were stirred and refluxed for 2 hours. Water (100ml) was added and the product was allowed to crystallise overnight. The crystals were removed by filtration and washed with water and dried to give 3-methyl-8-oximino-5,6,7,8-tetrahydroquinoline (27.5g) mp 188° C. Found: C,68.5; H,6.9; N,15.4, C10H12N2O requires C,68.2; H,6.9; N,15.1%.

Workup

  1. temperaturerefluxed for 2 hours
  2. customto crystallise overnight
  3. customThe crystals were removed by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9db2f02d70aa412d86fcac58dd0579df
Source dataset
uspto-grants-1976_11
Patent number
US03991065

Reaction notes

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