Ethyl 1-((4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)-1H-pyrazole-4-carboxylate → 1-((4-Methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)-1H-pyrazole-4-carboxylic acid

HRID 928424Notes

Reaction equation

[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][O:5][C:4]2[CH:9]=[CH:10][C:11]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([O:21]CC)=[O:20])[CH:16]=[N:15]3)=[CH:12][C:3]1=2>CO.[OH-].[Na+]>[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][O:5][C:4]2[CH:9]=[CH:10][C:11]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[N:15]3)=[CH:12][C:3]1=2

Participants

Conditions

Temperature: 20 °C

Procedure

Ethyl 1-((4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)-1H-pyrazole-4-carboxylate (780 mg, 0.618 mmol) was dissolved in a mixture of MeOH (5 ml) and 1N NaOH (5.00 ml). The reaction mixture was stirred for 2 hr at 20° C. and the MeOH was removed by evaporation under reduced pressure. The aqeuous phase was washed with AcOEt, then acidified with HCl and extracted with AcOEt. The organic layer was concentrated under reduced pressure to afford the title compound. HPLC (Method H) Rt=2.636 min; MS (Method A) [M−H]−=286.1

Workup

customthe MeOH was removed by evaporation under reduced pressure
washThe aqeuous phase was washed with AcOEt
extractionextracted with AcOEt
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-c9c03361c76146dfa6ca0d85a59a5958
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290485B2

Reaction notes

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