4-Ethoxy-2-nitroaniline → 6-Fluoro-N-(4-ethoxy-2-nitrophenyl)-3-pyridinecarboxamide
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH2:11]([O:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1)[CH3:12]>>[F:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:18][C:17]2[CH:19]=[CH:20][C:14]([O:13][CH2:11][CH3:12])=[CH:15][C:16]=2[N+:21]([O-:23])=[O:22])=[O:8])=[CH:9][CH:10]=1Participants
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).
Sources & evidence
- ORD record
- ord-b0d991d2df8d4c708e76d3d2f091f456
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06794397B2
Reaction notes
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