Ethyl 2-(2-(tert-butoxycarbonylamino)-6-methoxyphenyl)-2-oxoacetate → 4-methoxy-2,3-dihydro-1H-indole-2,3-dione
Reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[C:17](=[O:23])[C:18](OCC)=[O:19])=O)(C)(C)C>OS(O)(=O)=O>[CH3:16][O:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]2[C:10]=1[C:17](=[O:23])[C:18](=[O:19])[NH:8]2Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of ethyl 2-(2-(tert-butoxycarbonylamino)-6-methoxyphenyl)-2-oxoacetate (3.70 g, 110 mmol) and 10% H2SO4 (100 mL) was heated at 100° C. for 10 hours. After cooling down to ambient temperature, the reaction mixture was extracted with ether (3×100 mL). The combined ether solution was washed with water (2×50.0 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography to give 0.37 g (19%) of the title compound: MS (ES+) m/z 200.1 (M+23).
Workup
- temperatureAfter cooling down to ambient temperature
- extractionthe reaction mixture was extracted with ether (3×100 mL)
- washThe combined ether solution was washed with water (2×50.0 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo to dryness
Sources & evidence
- ORD record
- ord-14b8e1cd975c46718bac6ee7c9b0c499
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700641B2
Reaction notes
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