Methane → 2-Chlorohypoxanthine
Reaction equation
O.Cl.[Cl:3][C:4]1[NH:5][C:6](=[O:13])[C:7]2[NH:8][CH:9]=[N:10][C:11]=2[N:12]=1.[OH-].[Na+].C>O>[Cl:3][C:4]1[NH:5][C:6](=[O:13])[C:7]2[NH:8][CH:9]=[N:10][C:11]=2[N:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
180 g (0.80 mol) of 2-chlorohypoxanthine-hydrochloride-monohydrate are suspended in 3.6 liters of water and the pH is adjusted to 6.5 by the dropwise addition of concentrated sodium hydroxide solution. After heating to 60° C. the solution is treated with 18 g of decolorising charcoal and filtered. The filtrate is added dropwise to 300 ml of water, whilst a pH of 3.0 +/- 0.5 is maintained in the aqueous solution using 1N hydrochloric acid. The resulting suspension is cooled to 5°-10° C., suction filtered and the precipitate is washed with 0.5 liters of water at a temperature of +5° C. and with 300 ml of isopropanol. After drying at 50° C., 117 g (85.8% of theory) of the title compound are obtained in the form of a colourless crystal powder. By purifying via the sodium salt and re-liberation of the base, analytically pure material is obtained which is identical to the substance prepared from 2,6-dichloropurine according to J. A. Montgomery and L. B. Holum [J. Am. Chem. Soc. 79 (957) 2185].
Workup
- filtrationfiltered
- additionThe filtrate is added dropwise to 300 ml of water, whilst a pH of 3.0 +/- 0.5
- temperatureis maintained in the aqueous solution
- temperatureThe resulting suspension is cooled to 5°-10° C.
- filtrationsuction filtered
- washthe precipitate is washed with 0.5 liters of water at a temperature of +5° C. and with 300 ml of isopropanol
- customAfter drying at 50° C.
Sources & evidence
- ORD record
- ord-e5485da746d446939fcd07e9e942a705
- Source dataset
- uspto-grants-1993_11
- Patent number
- US05264573
Reaction notes
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