Water → 6-Fluoronicotinic Acid

HRID 1007197Notes

Reaction equation

HRID 1007197 reaction equation
[O-:1][Mn](=O)(=O)=O.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=1.[OH2:15]>>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:1])=[O:15])=[CH:10][N:9]=1

Participants

4

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 27746352-Fluoro-5-methylpyridine

Product 1

HCID 2428196-Fluoronicotinic Acid

Conditions

Temperature
100 °C

Procedure

To the solution of KMnO4 (284 mg, 1.8 mmol) in H2O (50 mL) was added 2-fluoro-5-methylpyridine (100 mg, 0.9 mmol) at room temperature. The reaction mixture was then heated to 100° C. for 4 h. The resulting precipitate was filtered and discarded. The aqueous solution was washed with 3:2, hexane: ethyl acetate (2×20 mL), acidified with 2N HCl, then extracted with ethyl acetate (3×20 mL). The organic extracts were combined and washed with H2O and brine, dried over anhydrous Na2SO4. The solvent was evaporated in vacuo to give 6-fluoronicotinic acid (30 mg) as a white solid. The title compound was prepared from 6-fluoronicotinic acid and 4-ethoxy-2-nitroaniline as a yellow solid as described in Example 15. 1H NMR (CDCl3): 11.09 (bs, 1H), 8.88 (d, J=2.4, 1H), 8.81 (d, J=9.3, 1H), 8.42-8.35 (m, 1H), 7.74 (d, J=3.3, 1H), 7.33-7.29 (m, 1H), 7.13-7.10 (m, 1H), 4.11 (q, J=7.2, 2H), 1.47 (t, J=7.2, 3H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washThe aqueous solution was washed with 3:2, hexane
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. washwashed with H2O and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d2c76ea1696644748ac6057e9938f08d
Source dataset
uspto-grants-2004_09
Patent number
US06794397B2

Reaction notes

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