Ammonium Acetate → 1-Amino-5-(5-fluoro-2-methylphenyl)cyclohexen-3-one

HRID 49191노트

반응식

HRID 49191 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[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+:21]>C(O)C>[NH2:21][C:12]1[CH2:13][CH:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[CH3:16])[CH2:9][C:10](=[O:15])[CH:11]=1

참가 물질

4

반응물 2

HCID 517165Ammonium AcetateHCID 183177715-(5-Fluoro-2-methylphenyl)cyclohexane-1,3-dione

생성물 1

HCID 183175171-Amino-5-(5-fluoro-2-methylphenyl)cyclohexen-3-one

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 5-(5-fluoro-2-methylphenyl)cyclohexane-1,3-dione (3.0 g) and ammonium acetate (3.1 g) in ethanol (50 ml) was heated under reflux for 14 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate, washed successively with water and saturated brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1-amino-5-(5-fluoro-2-methylphenyl)cyclohexen-3-one. This was dissolved in ethanol (70 ml) and toluene (120 ml), combined with 3-oxobutylaldehyde dimethyl acetal (4.1 g) and potassium hydroxide powder (0.57 g), and then heated under reflux. The mixture was combined with potassium hydroxide powder (0.12 g) after 30 minutes and with potassium hydroxide powder (0.12 g) and 3-oxobutylaldehyde dimethylacetal (0.33 g) after 1 hour and further with potassium hydroxide powder (0.12 g) after 1 hour and 30 minutes, and then stirred at the same temperature for 2 hours. After cooling, the solvent was distilled off under reduced pressure, and ethyl acetate was added. The organic layer was washed successively with water and saturated brine, and dried over magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the residue was subjected to a silica gel column (ethyl acetate-hexane) to obtain a crystal which was then recrystallized from ethyl acetate-hexane to obtain 7-(5-fluoro-2-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.5 g).

후처리

  1. temperatureunder reflux for 14 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-00bd0f7cf8484fffad328218735a325d
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706732B1

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