Phosphorus oxychloride → 4-Chloro-3-nitropyridine
Reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.O=P(Cl)(Cl)[Cl:9].O[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]>>[Cl:9][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]Participants
Conditions
- Temperature
- 140 °C
Procedure
In a reaction flask under nitrogen, were reacted at 70° C., 51.5 g of PCl5 and 75 ml of POCl3. At the same temperature was added carefully 34.6 g of (8). The temperature was increased to 140° C. and the reaction refluxed for 4 hours under nitrogen. To the cooled mixture, evaporated under vacuum, was added 100 ml of iced water. The pH was adjusted to 7.5 by the addition of granular sodium carbonate, and 60 ml of methylene chloride added and the mixture stirred vigorously until all the residue had completely dissolved. The phases were separated and the aqueous part was extracted with more methylene chloride (5×30 ml). The combined organic phases were treated with anhydrous sodium sulphate and evaporated to obtain 29.9 g of (9) as a yellow, waxy solid.
Workup
- customIn a reaction flask under nitrogen, were reacted at 70° C.
- temperaturethe reaction refluxed for 4 hours under nitrogen
- customTo the cooled mixture, evaporated under vacuum
- additionwas added 100 ml of iced water
- additionThe pH was adjusted to 7.5 by the addition of granular sodium carbonate, and 60 ml of methylene chloride
- additionadded
- dissolutionhad completely dissolved
- customThe phases were separated
- extractionthe aqueous part was extracted with more methylene chloride (5×30 ml)
- additionThe combined organic phases were treated with anhydrous sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-b5c1205b7b65447d8afea9b75fdff6e0
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07528252B2
Reaction notes
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