Water → HCID 84770249, compound
Reaction equation
[F:1][C:2]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][N:6]=1)([F:4])[CH3:3].[O-:12][Mn](=O)(=O)=O.[K+].[OH2:18]>>[F:4][C:2]([C:5]1[CH:10]=[C:9]([CH:8]=[CH:7][N:6]=1)[C:11]([OH:12])=[O:18])([F:1])[CH3:3]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
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).
Sources & evidence
- ORD record
- ord-ddab7e2c2c97499fbbf8dc39ccea8f44
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242969B2
Reaction notes
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