Sulfuric Acid → 2,6-Dichloro-5-fluoronicotinamide
Reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([F:10])=[C:4]([Cl:11])[N:3]=1.S(=O)(=O)(O)[OH:13]>>[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]([F:10])=[CH:6][C:7]=1[C:8]([NH2:9])=[O:13]Participants
3
Conditions
- Temperature
- 62.5 °C
Procedure
A suspension of 25 g (130.90 mmol) of 2,6-dichloro-5-fluoro-3-cyanopyridine in conc. sulfuric acid (125 ml) was stirred at 60-65° C. for 1 h. After cooling to RT, the contents of the flask were poured onto ice-water and extracted three times with ethyl acetate (100 ml each time). The combined organic phases were washed with water (100 ml) and then with saturated aqueous sodium hydrogencarbonate solution (100 ml), dried and concentrated on a rotary evaporator. The material obtained was dried under high vacuum.
Workup
- temperatureAfter cooling to RT
- additionthe contents of the flask were poured onto ice-water
- extractionextracted three times with ethyl acetate (100 ml each time)
- washThe combined organic phases were washed with water (100 ml)
- dry with materialwith saturated aqueous sodium hydrogencarbonate solution (100 ml), dried
- concentrationconcentrated on a rotary evaporator
- customThe material obtained
- customwas dried under high vacuum
Sources & evidence
- ORD record
- ord-4c552e517d324b67a49cc6f9842de255
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096592B2
Reaction notes
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