Ammonium Acetate → 1-Amino-5-(5-chloro-2-methoxyphenyl)cyclohexen-3-one

HRID 1700700ノート

反応式

HRID 1700700 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([CH:8]2[CH2:13][C:12](=O)[CH2:11][C:10](=[O:15])[CH2:9]2)[CH:7]=1.C([O-])(=O)C.[NH4+:22]>C(O)C>[NH2:22][C:12]1[CH2:13][CH:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:16][CH3:17])[CH2:9][C:10](=[O:15])[CH:11]=1

参加物

4

反応物 2

HCID 517165Ammonium AcetateHCID 183177015-(5-Chloro-2-methoxyphenyl)cyclohexane-1,3-dione

生成物 1

HCID 183173041-Amino-5-(5-chloro-2-methoxyphenyl)cyclohexen-3-one

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 5-(5-chloro-2-methoxyphenyl)cyclohexane-1,3-dione (5.0 g) and ammonium acetate (4.6 g) in ethanol (100 ml) was refluxed for 20 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 1-amino-5-(5-chloro-2-methoxyphenyl)cyclohexen-3-one, which was dissolved in ethanol (120 ml) and toluene (210 ml). To the solution were added 3-oxobutylaldehydedimethylacetal (6.5 g) and powdery potassium hydroxide (0.92 g), and the mixture was refluxed. To the mixture was added powdery potassium hydroxide (0.19 g), 30 minutes later; were added powdery potassium hydroxide (0.19 g) and 3-oxobutylaldehydedimethylacetal (0.52 g), 1 hour later; and was added powdery potassium hydroxide (0.19 g), 1.5 hours later, and 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) to give 7-(5-chloro-2-methoxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (2.2 g) as colorless crystals.

後処理

  1. customUnder reduced pressure, the solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with water and saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated

出典と根拠

ORDレコード
ord-76be2ecfc3a04318ae6173f22273c764
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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