5-Fluoronicotinic Acid → 2-Chloro-5-fluoronicotinic acid
Reaction equation
[Cl:1][C:2]1[N:10]=[C:9](Cl)[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].FC1C=NC=C(C=1)C(O)=O>>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]Participants
3
Procedure
Into a 200 mL round bottomed flask, 2,6-dichloro-5-fluoronicotinic acid (1 g), methanol (10 mL), triethylamine (0.96 g) and 5% Pd/calcium carbonate (one poisoned by lead) (107 mg) were charged under cooling with ice and stirred at room temperature for one hour in a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated to obtain a crude product (1.3 g). The concentrated filtrate was analyzed by HPLC and found to be a mixture comprising 26% of the title compound, 57% of 2,6-dichloro-5-fluoronicotinic acid and 17% of 5-fluoronicotinic acid.
Sources & evidence
- ORD record
- ord-5a07fb61943d4d028072376f71b788fa
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07414136B2
Reaction notes
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