Hydroxyamine hydrochloride → 4-(1,4-Dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)-2-furancarboxaldehyde oxime

HRID 1725089Notes

Reaction equation

HRID 1725089 reaction equation
[CH3:1][C:2]1([CH3:20])[O:7][C:6](=[O:8])[NH:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]3[CH:14]=[C:15]([CH:18]=O)[O:16][CH:17]=3)=[CH:12][C:3]1=2.Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>C(O)C>[CH3:1][C:2]1([CH3:20])[C:3]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]([CH:18]=[N:22][OH:23])[O:16][CH:17]=3)[CH:10]=[CH:9][C:4]=2[NH:5][C:6](=[O:8])[O:7]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 235096234-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-furan-2-carbaldehyde

Product 1

HCID 865850144-(1,4-Dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)-2-furancarboxaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-furan-2-carbaldehyde (2.7 g, 10 mmol), hydroxylamine hydrochloride (0.75 g, mmol) and sodium acetate (0.87 g, 10.6 mmol) was heated at reflux in 80% ethanol (25 mL) for 2 hours. The title compound crystallized from the cooled reaction mixture as tan crystals (1.5 g, 52.4%): mp 236-238° C. 1H NMR (DMSO-d6) δ 11.97 (s, 1H), 10.26 (s, 1H), 8.2 (s, 1H), 7.63 (s, 1H), 7.56-7.52 (m, 3H), 6.91-6.88 (d, 1 H, J=8.1 Hz), 1.66 (s, 6H). MS ESI m/z 285 [M−H]−. Anal. Calcd. For C15H14N2O4: C, 62.93; H, 4.93; N, 9.79. Found C, 62.77; H, 5.00; N, 9.79.

Workup

  1. temperaturewas heated
  2. customThe title compound crystallized from the cooled reaction mixture as tan crystals (1.5 g, 52.4%)

Sources & evidence

ORD record
ord-2f6eebaab9764d749ea9ed4d32b4267e
Source dataset
uspto-grants-2009_02
Patent number
US07488822B2

Reaction notes

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