Hydroxyamine hydrochloride → 1-hexyl-3-oximinomethyl-4-methoxy-6-methyl-2(1H)-quinolinone

HRID 36048Notes

Reaction equation

HRID 36048 reaction equation
[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([O:18][CH3:19])=[C:9]([CH:20]=O)[C:8]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl.[NH2:24][OH:25].C([O-])(=O)C.[Na+]>CO.O>[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([O:18][CH3:19])=[C:9]([CH:20]=[N:24][OH:25])[C:8]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 152333661-hexyl-3-formyl-4-methoxy-6-methyl-2(1H)-quinolinone

Product 1

HCID 731897501-hexyl-3-oximinomethyl-4-methoxy-6-methyl-2(1H)-quinolinone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-hexyl-3-formyl-4-methoxy-6-methyl-2(1H)-quinolinone (Step (2) of Example 1, 1 g), hydroxylamine hydrochloride (0.3 g) and sodium acetate (0.3 g) in methanol (20 ml) was stirred for 3hrs. The mixture was then diluted with water and extracted with methylene chloride. The extracts were dried, evaporated and the resulting solid was crystallized from ether-hexane to give 1 -hexyl-3-oximinomethyl-4-methoxy-6-methyl-2(1H)-quinolinone. That the expected product was obtained was confirmed by the spectral data: MS: m/e 316 (M+); NMR (CDCl3): δ3.98 (s, 3H, OCH3), 8.54 (s, 1H, CH=N).

Workup

  1. extractionextracted with methylene chloride
  2. customThe extracts were dried
  3. customevaporated
  4. customthe resulting solid was crystallized from ether-hexane

Sources & evidence

ORD record
ord-a40c1a07051a426abca2e4f03fe4e1e8
Source dataset
uspto-grants-1995_05
Patent number
US05412104

Reaction notes

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