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

HRID 660294Notes

Reaction equation

HRID 660294 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-3a8b0a5414df4f1ea2a15d5cb3184ba9
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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