Ammonia → 6-Bromopyridine-2-carboxamide

HRID 29262

Reaction equation

HRID 29262 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]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 219614086-Bromopyridine-2-carboxamideYield 45%

Reagents, catalysts & solvents 2

HCID 24386Thionyl ChlorideSolventHCID 312751,4-DioxaneSolvent

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

  1. temperatureThe reaction was cooled to room temperature
  2. customcondensed under reduced pressure
  3. customthe solvents were removed under reduced pressure
  4. 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

Linked notes

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