2,2,2-Trifluoroacetophenone → HCID 178498430, compound

HRID 874410Notes

Reaction equation

HRID 874410 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]([F:16])([F:15])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[CH3:17][O:18][C:19]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([NH2:27])[CH:22]=1)=[O:20].[OH-].[Na+]>N1C=CC=CC=1>[F:5][C:6]([F:16])([F:15])/[C:7](=[N:27]\[C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][N:24]=1)[C:19]([O:18][CH3:17])=[O:20])/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 99052,2,2-TrifluoroacetophenoneHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 236984Methyl 2-aminopyridine-4-carboxylate

Product 1

HCID 178498430HCID 178498430, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Thionyl chloride (2.2 ml) was added at 0° C. to a pyridine (4.8 ml) solution of 2,2,2-trifluoro-1-phenylethanone (5.1 g) and 2-aminopyridine-4-carboxylic acid methyl ester (4.5 g). The temperature of the reaction solution was increased to room temperature, and the reaction solution was then stirred for 1 hour. Thereafter, the reaction solution was poured into a 1 N sodium hydroxide aqueous solution, and the mixed solution was then extracted with ethyl acetate. Organic layers were gathered, and the gathered organic layer was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (silica gel: eluent; heptane:ethyl acetate=2:1-1:1), so as to obtain the title compound (2.5 g) in the form of a yellow liquid.

Workup

  1. extractionthe mixed solution was then extracted with ethyl acetate
  2. dry with materialthe gathered organic layer was then dried over anhydrous sodium sulfate
  3. distillationAfter that, the solvent was distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (silica gel: eluent; heptane:ethyl acetate=2:1-1:1)

Sources & evidence

ORD record
ord-177c681d117d4544a9ebcffe65ddb752
Source dataset
uspto-grants-2015_03
Patent number
US08980889B2

Reaction notes

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