Acetic Acid → HCID 178418543, compound
Reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].BrC1C=C(F)C(N)=C(F)C=1.C(O)(=[O:23])C>>[OH:23][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]Participants
Conditions
- Temperature
- 130 °C
Procedure
A mixture of 2-chloronicotinic acid (1.6 g, 10.15 mmol) and 4-bromo-2,6-difluoroaniline (3.24 g, 15.58 mmol) in acetic acid (40 ml) was heated overnight at 130° C. under nitrogen atmosphere. The mixture was cooled to room temperature to give a precipitate. The mixture was filtered, and the solid was rinsed with acetic acid to afford 2-hydroxynicotinic acid (side-product). A second solid precipitate when the filtrate was partially concentrated to give another precipitate which corresponds to N-(4-bromo-2,6-difluorophenyl)acetamide (another side-product). Finally the filtrate was concentrated to dryness and 3.14 g of the desired compound was obtained as a solid, containing some acetamide but the mixture was used to perform the next synthetic step.
Workup
- temperatureThe mixture was cooled to room temperature
- customto give a precipitate
- filtrationThe mixture was filtered
- washthe solid was rinsed with acetic acid
Sources & evidence
- ORD record
- ord-ffe0607f76b349dc9511588a8092e3f1
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258308B2
Reaction notes
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