Water → Ethyl 2-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-6-yl)propanoate

HRID 1626854Notes

Reaction equation

HRID 1626854 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[CH:10][C:11]=1[OH:12])=[O:4].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[O:4]=[C:3]1[CH2:2][O:12][C:11]2[CH:10]=[CH:9][C:8]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][C:6]=2[NH:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 57742174Ethyl 2-(3-(2-chloroacetamido)-4-hydroxyphenyl)propanoate

Product 1

HCID 57742190Ethyl 2-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-6-yl)propanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 2-(3-(2-chloroacetamido)-4-hydroxyphenyl)propanoate (100 mg, 0.350 mmol) in acetone (10 mL) was added potassium carbonate (59 mg) at room temperature and refluxed for 3 hours. The reaction mixture was cooled to room temperature and added water (15 mL). The mixture was extracted with EtOAc. The organic layer was dried with MgSO4 and filtered. EtOAc was removed by evaporation. The residue was purified by column chromatography eluting with n-Hexane/EtOAc=2/1.

Workup

  1. temperaturerefluxed for 3 hours
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customEtOAc was removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with n-Hexane/EtOAc=2/1

Sources & evidence

ORD record
ord-5dce97a2377a4700a776898082a5a3e3
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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