Potassium Hydroxide → 7-(2-Fluoro-5-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

HRID 1700697ノート

反応式

HRID 1700697 の反応式
[NH2:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[F:15])[CH2:5][C:4](=[O:16])[CH:3]=1.[OH-].[K+]>C(O)C.C1(C)C=CC=CC=1>[F:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[CH:6]1[CH2:7][C:2]2[N:1]=[CH:7][CH:2]=[C:3]([CH3:4])[C:3]=2[C:4](=[O:16])[CH2:5]1

参加物

5

反応物 2

HCID 14797Potassium Hydroxide4 回HCID 183176231-Amino-5-(2-fluoro-5-methylphenyl)cyclohexen-3-one

生成物 1

HCID 183175417-(2-Fluoro-5-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one収率 162.8%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

In ethanol (35 ml) and toluene (60 ml) was dissolved 1-amino-5-(2-fluoro-5-methylphenyl)cyclohexen-3-one (1.3 g), and to the solution were added 3-oxobutylaldehydedimethylacetal (2.0 g) and powdery potassium hydroxide (0.32 g). The mixture was refluxed, and to the mixture was added powdery potassium hydroxide (0.07 g), 30 minutes later; were added powdery potassium hydroxide (0.07 g) and 3-oxobutylaldehydedimethylacetal (0.16 g), 1 hour later; and was added powdery potassium hydroxide (0.07 g), 1.5 hours later. The mixture was stirred at the same temperature for 2 hours and cooled. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, ethyl acetate was evaporated, and the residue was purified with silica gel column (ethyl acetate-hexane). The resulting crystals were recrystallized from ethyl acetate-hexane to give 7-(2-fluoro-5-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.3 g).

後処理

  1. temperatureThe mixture was refluxed
  2. temperaturecooled
  3. customUnder reduced pressure, the solvent was evaporated
  4. additionto the residue was added ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customUnder reduced pressure, ethyl acetate was evaporated
  8. customthe residue was purified with silica gel column (ethyl acetate-hexane)
  9. customThe resulting crystals were recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-f690bbdecb884395aa396e160421c467
出典データセット
uspto-grants-2002_02
特許番号
US06350749B1

反応ノート

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