Hydrochloric Acid → 2-(2-Methoxybenzoyl)-3-methylpyridine

HRID 892508Notes

Reaction equation

HRID 892508 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Mg].[C:11]([C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]=1)#N.Cl.[OH-:21].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:19][C:18]1[C:13]([C:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])=[O:21])=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 113582-BromoanisoleHCID 14798Sodium HydroxideHCID 8199283-Methylpyridine-2-carbonitrileHCID 5462224Magnesium

Product 1

HCID 198956902-(2-Methoxybenzoyl)-3-methylpyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

35.5 g of o-bromoanisole were added dropwise to 5.71 g of magnesium turnings covered with 50 ml of tetrahydrofuran while heating to maintain reflux. 15 minutes after completion of the addition 14.93 g of 2-cyano-3-methylpyridine in 150 ml of tetrahydrofuran were added dropwise without further heating. After 1 hour at room temperature dilute hydrochloric acid and ethyl acetate were added followed by dilute sodium hydroxide solution to pH 14. The mixture was extracted with ethyl acetate, the organic extract was dried over sodium sulphate and then evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:3) and then ethyl acetate/petroleum ether (1:2) for the elution. There were obtained 9.81 g of 2-methoxyphenyl 3-methyl-2-pyridyl ketone in the form of a solid of melting point 98°-100° C.

Workup

  1. temperaturewhile heating
  2. temperatureto maintain
  3. temperaturereflux
  4. additionwere added dropwise without further heating
  5. extractionThe mixture was extracted with ethyl acetate
  6. extractionthe organic extract
  7. dry with materialwas dried over sodium sulphate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel
  10. washethyl acetate/petroleum ether (1:2) for the elution

Sources & evidence

ORD record
ord-f9c8fd77104b4730a33025aa1ec7abef
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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