Ammonia → 6-Bromopyridine-2-carboxamide
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[NH3:11]>S(Cl)(Cl)=O.O1CCOCC1>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH2:11])=[O:10])[CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
6-Bromopicolinic acid (1000 mg, 4.95 mmol) was suspended in thionyl chloride (15 mL) and heated at 70° C. for 5 h. The reaction was cooled to room temperature and the volatiles were condensed under reduced pressure. A solution of ammonia (2M in dioxane (15 mL) was added to the residue and then the solvents were removed under reduced pressure. The crude residue was purified by MPLC with a gradient of 0 to 20% MeOH/dichloromethane to give 6-Bromo-pyridine-2-carboxylic acid amide as a white powder (555 mg, 45%). MS ES (MH+=201.0/203.0).
Workup
- temperatureThe reaction was cooled to room temperature
- customcondensed under reduced pressure
- customthe solvents were removed under reduced pressure
- customThe crude residue was purified by MPLC with a gradient of 0 to 20% MeOH/dichloromethane
Sources & evidence
- ORD record
- ord-c44d8a796e344fa9ab518435508d9ef8
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420066B2
Reaction notes
Loading…