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

HRID 1073871ノート

反応式

HRID 1073871 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-36fbf6b4794d46ea8a75f6768867873a
出典データセット
uspto-grants-1990_11
特許番号
US04971982

反応ノート

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