O-Toluidine → Quinoline

HRID 1534480ノート

反応式

HRID 1534480 の反応式
C([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2COC(=O)C1C=CC=CC=1)(=O)C(C)C.CC1C=CC=CC=1N>O1CCOCC1>[N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 7242O-ToluidineHCID 10384366HCID 10384366、化合物

生成物 1

HCID 7047Quinoline収率 113%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A solution of 3-isobutyryl-4-chloro-8-benzoyloxymethylquinoline (3.68 g, 10 mmol) and 2-methylaniline (2.13 ml, 20 mmol) in dioxan (50 ml) was heated at reflux for 2 hours, then evaporated, taken up in dichloromethane, washed with aqueous sodium bicarbonate, water and brine, dried and evaporated to an oil. This was taken up in 1% methanolic sodium hydroxide solution (100 ml) and stirred vigorously for 1 hour. The methanol was evaporated, water and dichloromethane added, the aqueous phase adjusted to pH 10 and extracted with dichloromethane. The organic extracts were dried, evaporated and chromatographed (silica, gel, 1%-2% methanol in dichloromethane). Trituration of the product fractions with ether followed by recrystallization from aqueous methanol gave 3-isobutyryl-4-(2-methylphenylamino)-8-hydroxymethyl)quinoline (1.46 g, 44%), m.p. 116°-118°.

後処理

  1. temperatureat reflux for 2 hours
  2. customevaporated
  3. washwashed with aqueous sodium bicarbonate, water and brine
  4. customdried
  5. customevaporated to an oil
  6. customThe methanol was evaporated
  7. additionwater and dichloromethane added
  8. extractionextracted with dichloromethane
  9. customThe organic extracts were dried
  10. customevaporated
  11. customchromatographed (silica, gel, 1%-2% methanol in dichloromethane)
  12. customTrituration of the product fractions with ether followed by recrystallization from aqueous methanol

出典と根拠

ORDレコード
ord-01912ff5ffe342eda9c9505db63865b4
出典データセット
uspto-grants-1992_02
特許番号
US05089504

反応ノート

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