Acetic Acid → 2-(3,4-Dihydro-3-oxo-2H-benzo[b][1,4]oxazin-6-yl)propanoic acid

HRID 660295Notes

Reaction equation

HRID 660295 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([CH:12]([CH3:18])[C:13]([O:15]CC)=[O:14])=[CH:11][C:4]=2[NH:3]1.[OH-].[Na+].O.C(O)(=O)C>CCO>[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([CH:12]([CH3:18])[C:13]([OH:15])=[O:14])=[CH:11][C:4]=2[NH:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 57742190Ethyl 2-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-6-yl)propanoate

Product 1

HCID 577421472-(3,4-Dihydro-3-oxo-2H-benzo[b][1,4]oxazin-6-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-6-yl)propanoate (63 mg, 0.253 mmol) in 90% aq. EtOH (4.5 mL) was added sodium hydroxide (50 mg, 1.25 mmol) at room temperature. The reaction mixture was stirred for 12 hours at 50° C. and cooled to room temperature. The mixture was added water (20 mL) and acidified with acetic acid. The mixture was extracted with methylene chloride. The organic layer was dried with MgSO4 and filtered. The filtrate was concentrated in vacuo.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-803f88faff8a41189e5d409f40da2a6d
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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