Ethanol → HCID 136074473, compound

HRID 1609006Notes

Reaction equation

HRID 1609006 reaction equation
C(O)C.[C:4]([C:8]1[C:9](=[O:30])[CH2:10][CH:11]([C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][C:21](=[O:24])[N:20]([CH2:25][CH2:26][CH2:27][Cl:28])[C:19]=3[CH:29]=2)[CH2:12][C:13]=1[OH:14])(=O)[CH2:5][CH3:6].Cl.[CH2:32]([O:34][NH2:35])[CH3:33].C([O-])(=O)C.[Na+]>O.CC(C)=O.CCCCCC>[CH2:32]([O:34][N:35]=[C:4]([C:8]1[C:9](=[O:30])[CH2:10][CH:11]([C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][C:21](=[O:24])[N:20]([CH2:25][CH2:26][CH2:27][Cl:28])[C:19]=3[CH:29]=2)[CH2:12][C:13]=1[OH:14])[CH2:5][CH3:6])[CH3:33]

Participants

7

Reactant 4

HCID 702EthanolHCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178458820HCID 178458820, compound

Product 1

HCID 136074473HCID 136074473, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21880519Acetone hexaneSolvent

Procedure

To 50 mL of absolute ethanol were added in sequence 1.6 g (4.1 mmol) of 2-propionyl-3-hydroxy-5-(N-(3-chloropropyl)-3-oxo-(2H)-1,4-benzoxazin-6-yl)-cyclohex-2-en-1-one, 0.32 g (3.4 mmol) of ethoxyamine hydrochloride and 0.27 g (3.3 mmol) of anhydrous sodium acetate. The resulting mixture was stirred at ambient temperature for 2.5 hours. The reaction mixture was then diluted with 200 mL of water and extracted twice with 50 mL portions of dichloromethane. The extracts were combined, dried over MgSO4 and filtered. Evaporation off of the solvent gave the crude product as a yellow oily residue. Flash chromatography on silica gel eluting with 20 percent acetone/hexane afforded the above-named product as a pale glassy oil in a yield of 1.0 g (56 percent of theoretical). 1H NMR (CDCl3): d1.05-1.43 (m, 6H, both --CH2CH3 's), 2.15 (p, J=7 Hz, 2H,--CH2CH2Cl and --CH2Cl), 4.57 (s, 2H, --OCH2C=O), 6.83-7.00 (m, 3H, aromatic H's), 14.9 (broad s, 1H, enol H); (Compound 9).

Workup

  1. extractionextracted twice with 50 mL portions of dichloromethane
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customEvaporation off of the solvent
  5. customgave the crude product as a yellow oily residue

Sources & evidence

ORD record
ord-53c2454f556147d5909b87ac1e666d93
Source dataset
uspto-grants-1995_03
Patent number
US05399542

Reaction notes

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