Acetone → Ethyl 4-hydroxy-1-methyl-2-oxo-7-(trifluoromethyl)-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1801984Notes

Reaction equation

HRID 1801984 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.Cl[C:17]1[N:25]=[C:24](C(F)(F)F)C=C[C:18]=1[C:19]([OH:21])=[O:20].C([O-])([O-])=[O:31].[K+].[K+].IC.[CH3:38][C:39](C)=O>>[OH:6][C:4]1[C:3]2[C:2](=[N:11][C:10]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:8]=2)[N:25]([CH3:24])[C:17](=[O:31])[C:18]=1[C:19]([O:21][CH2:38][CH3:39])=[O:20]

Participants

6

Reactant 5

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27782102-Chloro-6-(trifluoromethyl)nicotinic acidHCID 46311111Methyl 2-chloro-6-(trifluoromethyl)pyridine-3-carboxylate

Product 1

HCID 57671568Ethyl 4-hydroxy-1-methyl-2-oxo-7-(trifluoromethyl)-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Procedure

Methyl 2-chloro-6-(trifluoromethyl)nicotinate. To a mixture of 2-chloro-6-(trifluoromethyl)nicotinic acid (available from Fluorochem Products, West Columbia, S.C.) (6.66 g) and K2CO3 (15.7 g, 114 mmol) in acetone (125 mL) was added iodomethane (2.60 mL, 41.7 mmol) dropwise with stirring at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at 35° C. for 18 hours and was then filtered through a plug of Celite®. The filtrate was evaporated under reduced pressure to give the title compound. MS (ESI, pos. ion) m/z: 240 (M+1).

Workup

  1. stirringThe reaction mixture was stirred at 35° C. for 18 hours
  2. filtrationwas then filtered through a plug of Celite®
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e8eacfb290e54e9297a0bcb0d22bbc33
Source dataset
uspto-grants-2013_01
Patent number
US08349868B2

Reaction notes

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