Anisole → 2-Hydroxyisonicotinic Acid
Reaction equation
COC1C=CC(C[O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][N:17]=2)[C:12]([OH:14])=[O:13])=CC=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[O:8]=[C:9]1[CH:10]=[C:11]([C:12]([OH:14])=[O:13])[CH:15]=[CH:16][NH:17]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Compound 1 (20.4 g, 84.0 mmol) obtained in Reference Example 12 was dissolved in trifluoroacetic acid (168 mL), and anisole (91.1 mL, 0.840 mol) was added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was reslurried with ethyl acetate to afford 2-oxo-1,2-dihydropyridine-4-carboxylic acid (6.99 g, 60%) as a white solid.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5d1248951b5c4c9dae895dfe8443f63c
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420827B2
Reaction notes
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