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

HRID 1626855Notes

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

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. white solid (m.p. 191-193° C.), yield: 95%,

Workup

temperaturecooled to room temperature
extractionThe mixture was extracted with methylene chloride
dry with materialThe organic layer was dried with MgSO4
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-9c56c6063471497f85b038705f6d6ca8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785474B2

Reaction notes

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