Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Permanganate | HCID 516875 | — |
| Reactant | Pyridine, 2-(1,1-difluoroethyl)-4-methyl- | HCID 71299907 | — |
| Product | HCID 84770249 | HCID 84770249 | 12% |
Reaction Steps
To a solution of 2-(1,1-difluoroethyl)-4-methylpyridine (1 equiv.) in water (2.0 M) was added KMnO4 (3.0 equiv) and heated to 80° C. for 4 hrs. LCMS analysis indicated the formation of the desired product (MH+—188.0, Rt—0.52 min). The reaction was acidified to pH 3 with 1M HCl. The white precipitate was filtered and dried. Isolated 2-(1,1-difluoroethyl)isonicotinic acid in 12% yield. LCMS (m/z) (M+H)=188.0, Rt=0.52). 1H NMR (400 MHz, <cd3od>) δ ppm 2.01 (t, J=18.78 Hz, 3H) 8.00 (d, J=4.70 Hz, 1H) 8.16 (s, 1H) 8.80 (d, J=5.09 Hz, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09242969B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-ddab7e2c2c97499fbbf8dc39ccea8f44 |
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| Source note | uspto-grants-2016_01 |
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