Anisole → 2-Hydroxyisonicotinic Acid

HRID 337542Notes

Reaction equation

HRID 337542 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]1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 23144786HCID 23144786, compound

Product 1

HCID 2807562-Hydroxyisonicotinic AcidYield 60%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

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

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b0cb81c6ee494e998bec5b9400365f93
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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