Acetic Acid → 1-Oxo-1,2-dihydronaphtho[1,8-cd]azepine-3-carboxylic Acid Methyl Ester
Reaction equation
COC(=O)[CH:4]([N+:19]([O-])=O)[CH:5]1[C:14]2[C:9]3[C:10](=[CH:15][CH:16]=[CH:17][C:8]=3[C:7](=O)O1)[CH:11]=[CH:12][CH:13]=2.C(O)(=[O:25])C.[C:27]([O:30][CH2:31]C)(=[O:29])C>CCO.[Fe]>[CH3:31][O:30][C:27]([C:17]1[CH2:16][C:15](=[O:25])[C:10]2[C:9]3[C:8]=1[CH:7]=[N:19][CH:4]=[CH:5][C:14]=3[CH:13]=[CH:12][CH:11]=2)=[O:29]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of nitro-(3-oxo-1H,3H-benzo[de]isochromen-1-yl)-acetic acid methyl ester (1.05 g, 3.33 mmol) in EtOH (12 mL) is added acetic acid (4 mL) followed by Fe (560 mg, 10 mmol) and the mixture is stirred at 100° C. for 90 min. Ethyl acetate is added to the mixture and any insoluble material is filtered. The filtrate is washed with water and the organic phase is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 0-50% EtOAc/hexane as eluent to give the title compound.
Workup
- filtrationany insoluble material is filtered
- washThe filtrate is washed with water
- dry with materialthe organic phase is dried over magnesium sulfate
- customThe solvent is removed under reduced pressure
- customthe residue purified by flash chromatography
Sources & evidence
- ORD record
- ord-13cbd95fa7284e34aaf32568c956e558
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084448B2
Reaction notes
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