Potassium Carbonate → 6-(2-Fluoro-4-formyl-6-methoxy-phenoxy)-nicotinonitrile

HRID 228416Notes

Reaction equation

HRID 228416 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10])[CH:5]=[O:6].Cl[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[O:10][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 5984523-Fluoro-4-hydroxy-5-methoxybenzaldehydeHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 859574866-(2-Fluoro-4-formyl-6-methoxy-phenoxy)-nicotinonitrileYield 66.9%

Procedure

Using a method similar to Example 710, Step 2, using 3-fluoro-4-hydroxy-5-methoxy-benzaldehyde (Journal of Organic Chemistry (1986), 51(2H), 4072-3.) (2.84 g, 16.7 mmol), 6-chloronicotinonitrile (2.31 g, 16.7 mmol) and K2CO3 (3.46 g, 25.0 mmol) gives 6-(2-fluoro-4-formyl-6-methoxy-phenoxy)-nicotinonitrile (3.04 g) as a white solid. 1HNMR (CDCl3): 9.94 (s, 1H), 8.37 (s, 1H), 7.98 (d, 1H), 7.36 (m, 2H), 7.20 (d, 1H), 3.87 (s, 3H).

Sources & evidence

ORD record
ord-db98eabd7523483d852d5b52ac8cd324
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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