O-ethylhydroxylamine hydrochloride → HCID 136401233, compound

HRID 1609003Notes

Reaction equation

HRID 1609003 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][CH:23]=[CH2:24])[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+]>CS(C)=O.O>[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][CH:23]=[CH2:24])[C:16]=3[CH:25]=2)[CH2:9][C:10]=1[OH:11])[CH2:2][CH3:3])[CH3:29]

Participants

6

Reactant 3

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178456565HCID 178456565, compound

Product 1

HCID 136401233HCID 136401233, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 1.3 g (3.7 mmol) of 2-propionyl-3-hydroxy-5-(N-(2-propenyl)-3-oxo-(2H)-1,4-benzoxazin-6-yl)cyclohex-2-en-1-one in 20 mL of methyl sulfoxide was treated with 0.43 g (4.5 mmol) of ethoxyamine hydrochloride and 0.36 g (4.4 mmol) of anhydrous sodium acetate. The resulting mixture was stirred at ambient temperature under a nitrogen atmosphere for 6 hours. The reaction mixture was diluted with 200 mL of water and extracted thrice with 20 mL portions of diethylether. The extracts were combined, washed with water, then aqueous sodium chloride, dried over MgSO4 and filtered. Evaporation off of the solvent gave the crude product as a yellow oil which solidified upon standing. The resulting glassy solid was dissolved in a warm 1:1 ether-hexane solution. On cooling, the compound oiled out of the solution and again solidified and was isolated by filtration as a light tan solid. The product was recovered in a yield of 1.1 g (75 percent of theoretical) and melted at 79°-83° C.; 1H NMR(CDCl3): d1.12 (t, J=7 Hz, 3H,--CCH2CH3), 1.32 (t, J=7 Hz, 3H,--OCH2CH3), 2.55-3.55 (m, 7H), 4.16 (q, J=7 Hz, 2H,--OCH2CH3), 4.50-4.70 (m including s at 4.60 for OCH2C=O, 4H, --N--CH2), 5.10-5.42 (m, 2H,--OCH=CH3), 4.70 (s, 2H, --OCH2C=O), 4.88 (s, 2H, --NCH2CN), 6.92-7.20 (m, 3H, aromatic H's), 15.10 (broad s, 1H, enol H); (Compound 5).

Workup

  1. extractionextracted thrice with 20 mL portions of diethylether
  2. washwashed with water
  3. dry with materialaqueous sodium chloride, dried over MgSO4
  4. filtrationfiltered
  5. customEvaporation off of the solvent

Sources & evidence

ORD record
ord-652a4fa87c74443ba8fd961e14cc47f1
Source dataset
uspto-grants-1995_03
Patent number
US05399542

Reaction notes

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