Acetonitrile → HCID 178421665, compound

HRID 1737146Notes

Reaction equation

[OH:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.S(O[O-])([O-])(=O)=O.[NH4+].[NH4+].[C:22](#N)[CH3:23]>O.C(OCC)C.[N+]([O-])([O-])=O.[Ag+]>[OH:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[C:11]=1[C:22]1([CH3:23])[CH2:10][CH2:11][CH2:2][CH2:3]1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

Conditions

Temperature: 20 °C

Procedure

A 50% excess of this acid was added to a stirred solution of 2-hydroxynaphthalene-1,4-dione (1.00 g, 5.7 mmol), and silver nitrate (600 mg) in a mixture of acetonitrile (20 ml) and water (20 ml) at 65° C. and a solution of ammonium peroxysulphate (1.96 g, 8.6 mmol) in water (10 ml) was slowly added to that over a period of 15 minutes. The mixture was heated for a further hour before cooling to room temperature (about 20° C.) and diluting with diethyl ether (50 ml). The organic phase was separated and washed successively with 25 water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution before drying over magnesium sulphate as set out in Example 3. Filtration and evaporation of the solvent under reduced pressure followed by silica gel column chromatography using 2:1 petrol:diethyl ether as eluant gave 2-hydroxy-3-(1-methylcyclopentyl)naphthalene-1,4-dione (mp 116-118° C.).

Workup

temperatureThe mixture was heated for a further hour
customThe organic phase was separated
washwashed successively with 25 water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution
dry with materialbefore drying over magnesium sulphate
filtrationFiltration and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-6b7f9a07a2384d09985199932e760a08
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05962002

Reaction notes

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