Pyridine → HCID 59553705, compound

HRID 1170938Notes

Reaction equation

HRID 1170938 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](Cl)=[O:12])=[CH:5][CH:4]=1.Cl.[CH3:17][NH:18][O:19][CH3:20].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:20][O:19][N:18]([CH3:17])[C:11](=[O:12])[CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 10331694HCID 10331694, compound

Product 1

HCID 59553705HCID 59553705, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 3.034 g (13 mmol) 3-(4-Trifluoromethyl-phenyl)-propionyl chloride (CAS: 539855-79-3) and 1.4 g (14.1 mmol) N,O-Dimethylhydroxylamine hydrochloride in 55 mLl chloroform, under argon, was added dropwise 2.28 mL (28 mmol) pyridine at 0° C. The solution was allowed to warm to RT and was stirred for 2 hour. The mixture was washed with 1N HCl (50 mL). The organic layer was washed once with 1N NaOH. The organic phases was dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was purified with flash column chromatography on silica gel eluting with a gradient formed from heptane and ethylacetate to provide 2.1 g (63%) of title compound as colorless oil. MS (m/e): 262.0 (MH+).

Workup

  1. washThe mixture was washed with 1N HCl (50 mL)
  2. washThe organic layer was washed once with 1N NaOH
  3. dry with materialThe organic phases was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe crude oil was purified with flash column chromatography on silica gel eluting with a gradient
  7. customformed from heptane and ethylacetate

Sources & evidence

ORD record
ord-ddc63fe5fb524fdc83a943cee92082ef
Source dataset
uspto-grants-2010_11
Patent number
US07829563B2

Reaction notes

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