O-ethylhydroxylamine hydrochloride → HCID 136018157, compound

HRID 1609005Notes

Reaction equation

HRID 1609005 reaction equation
[C:1]([C:5]1[C:6](=[O:26])[CH2:7][CH:8]([C:12]2[CH:13]=[CH:14][C:15]3[O:20][CH2:19][C:18](=[O:21])[N:17]([CH2:22][O:23][CH3:24])[C:16]=3[CH:25]=2)[CH2:9][C:10]=1[OH:11])(=O)[CH2:2][CH3:3].Cl.[CH2:28]([O:30][NH2:31])[CH3:29].C([O-])(=O)C.[Na+]>C(O)C>[CH2:28]([O:30][N:31]=[C:1]([C:5]1[C:6](=[O:26])[CH2:7][CH:8]([C:12]2[CH:13]=[CH:14][C:15]3[O:20][CH2:19][C:18](=[O:21])[N:17]([CH2:22][O:23][CH3:24])[C:16]=3[CH:25]=2)[CH2:9][C:10]=1[OH:11])[CH2:2][CH3:3])[CH3:29]

Participants

5

Reactant 3

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178458823HCID 178458823, compound

Product 1

HCID 136018157HCID 136018157, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 40 mL of absolute ethanol were added in sequence 0.90 g (2.5 mmol) of 2-propionyl-3-hydroxy-5-(N-methoxymethyl-3-oxo-(2H)-1,4 benzoxazin-6-yl)-cyclohex-2-en-1-one, 0.31 g (3.2 mmol) of ethoxyamine hydrochloride and 0.26 g (3.2 mmol) of anhydrous sodium acetate. The resulting mixture was stirred at ambient temperature for 3 hours. The reaction mixture was then partitioned between 200 mL of water and 50 mL of dichloromethane. The organic layer was separated, dried over MgSO4 and filtered. Evaporation off of the solvent gave the crude product as an oily residue which crystallized upon standing. The crude solid was triturated in warm ether and the above-named product was isolated by filtration as a white solid which melted at 101°-103° C. in a yield of 0.60 g (60 percent of theoretical). 1H NMR (CDCl3): d1.05-1.52 (m, 6H, both --CH2CH3 's), 2.58-3.65 (m including 2H,OCH2C=0), 5.33 (s, 2H, --NCH2O), 6.85-7.30 (m, 3H, aromatic H's), 15.05 (broad s, 1H, enol H); (Compound 8).

Workup

  1. customThe reaction mixture was then partitioned between 200 mL of water and 50 mL of dichloromethane
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customEvaporation off of the solvent

Sources & evidence

ORD record
ord-d45411a9ec4d496b9dee8196f9f4d6b2
Source dataset
uspto-grants-1995_03
Patent number
US05399542

Reaction notes

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