Methanol → methyl2-(7-amino-4-methyl-2-oxo-2H-chromen-3-yl)acetate

HRID 2369748

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:17])=[C:7]([CH2:13][C:14]([OH:16])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[CH3:18]O>OS(O)(=O)=O>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:17])=[C:7]([CH2:13][C:14]([O:16][CH3:18])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

7-Amino-4-methyl-3-coumarinylacetic acid (43.1 mg, 0.18 mmol) was dissolved in MeOH (40 ml). H2SO4 (5 drops) was added, and the reaction mixture was heated to 120° C. and stirred. After 4 hr, the disappearance of the starting materials was confirmed, and the reaction mixture was cooled to room temperature. The reaction mixture was concentrated to ⅓ and the mixture was neutralized with aqueous saturated NaHCO3 solution. The reaction mixture was extracted with BuOH, and the organic layer was concentrated. The residue was purified by silica gel column chromatography (eluate: hexane:EtOAc=1:2) to give the object compound (34.4 mg, 0.14 mmol, 75%).

Workup

temperaturethe reaction mixture was cooled to room temperature
concentrationThe reaction mixture was concentrated
extractionThe reaction mixture was extracted with BuOH
concentrationthe organic layer was concentrated
customThe residue was purified by silica gel column chromatography (eluate: hexane:EtOAc=1:2)

Sources & evidence

ORD record: ord-3954169c5b93459d91dc616754cf0221
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08709721B2

Linked notes

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