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

HRID 2071602Notes

Reaction equation

HRID 2071602 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:6](=O)[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.Cl.[NH2:14][OH:15].[OH-].[Na+].C(O)C>O>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:6](=[N:14][OH:15])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 123582233-Methyl-6,7-dihydroquinolin-8(5H)-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The quinoline (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.

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-bad60323c8ff471fa2c71be304bfaeb8
Source dataset
uspto-grants-1977_09
Patent number
US04048175

Reaction notes

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