Ethanol → HCID 14579592, compound
Reaction equation
[F:1][C:2]1[CH:14]=[C:13]([F:15])[C:12]2[C:11]3[C:6](=[CH:7][C:8]([F:18])=[CH:9][C:10]=3[O:16][CH3:17])[C:5](=O)[C:4]=2[CH:3]=1.[C-]#N.[K+].[C:23](=[O:26])([O-])[O-].[NH4+:27].[NH4+:28].[CH2:29]([OH:31])C>>[F:1][C:2]1[CH:14]=[C:13]([F:15])[C:12]2[C:11]3[C:6]([C:5]4([C:29](=[O:31])[NH:28][C:23](=[O:26])[NH:27]4)[C:4]=2[CH:3]=1)=[CH:7][C:8]([F:18])=[CH:9][C:10]=3[O:16][CH3:17]Participants
Conditions
- Temperature
- 115 °C
Procedure
A mixture of 2,4,7-trifluoro-5-methoxy-9H-fluoren-9-one (2.0 g, 7.6 mmol), potassium cyanide (3 eq, 23 mmol, 1.5 g), and ammonium carbonate (4 eq, 30 mmol, 2.9 g) in 50 mL of ethanol was heated in a sealed bomb at 115° C. for 24 h. After the bomb was cooled and opened, the solvent was evaporated and the residue dissolved in 1M aqueous sodium hydroxide. The basic solution was extracted with ethyl acetate to remove base insoluble impurities and then acidified using concentrated hydrochloric acid. The acidic solution was extracted with ethyl acetate and the extracts were dried over MgSO4 and concentrated to leave 1.2 g of a brown solid. Chromatography on silica gel using 45% ethyl acetate in hexane provided 500 mg (20%) of the spirohydantoin: mp 227°-229° C.
Workup
- temperatureAfter the bomb was cooled
- customthe solvent was evaporated
- dissolutionthe residue dissolved in 1M aqueous sodium hydroxide
- extractionThe basic solution was extracted with ethyl acetate
- customto remove base insoluble impurities
- extractionThe acidic solution was extracted with ethyl acetate
- dry with materialthe extracts were dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8102621779f04f86a9979b91fd8448fc
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04864028
Reaction notes
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