Water → 7-Hydroxy-4-hydroxyimino-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

HRID 370044Notes

Reaction equation

HRID 370044 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[C:9](=O)[CH2:8][CH:7]1[CH3:20])=[O:5])[CH3:2].Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[C:9](=[N:22][OH:23])[CH2:8][CH:7]1[CH3:20])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 544378587-Hydroxy-6-methoxy-2-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

Product 1

HCID 1363337157-Hydroxy-4-hydroxyimino-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-Hydroxy-6-methoxy-2-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (5.10 g, 18.3 mmol) was dissolved in ethanol (100 mL), and hydroxylamine hydrochloride (3.81 g, 54.8 mmol) was added, followed by sodium acetate (3.74 g, 45.7 mmol). The mixture was heated at reflux for 2 h and then left to stand at room temperature overnight. Water (100 mL) was added, and the volatiles were removed in vacuo to give a yellow slurry. This slurry was filtered and washed with water to give the title compound as a fine powder (4.755 g, 89%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. waitleft
  4. customthe volatiles were removed in vacuo
  5. customto give a yellow slurry
  6. filtrationThis slurry was filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-7dac08032c514b008419b179c0e64cfb
Source dataset
uspto-grants-2000_10
Patent number
US06140342

Reaction notes

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