Acetic Acid → [1-(2-Methoxyphenyl)methylidene]-(2-methylquinolin-5-yl)amine

HRID 1921577

反応式

HRID 1921577 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O.C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[N:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2

参加物

5

反応物 3

HCID 176Acetic AcidHCID 86582-MethoxybenzaldehydeHCID 1486835-Quinolinamine, 2-methyl-

生成物 1

HCID 67136395[1-(2-Methoxyphenyl)methylidene]-(2-methylquinolin-5-yl)amine収率 118.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To 1.74 g (11 mmol) 5-amino-2-methylquinolin and 1.33 ml (11 mmol) 2-methoxybenzaldehyde in 33 ml toluene are added 50 μl acetic acid and 2 g molecular sieve. The mixture is heated over 2 hours under reflux and filtrated through a path of cellites after cooling. The solvent is evaporated and the residue is two times azeothrophed with small portions of toluene. 3.6 g of [1-(2-methoxyphenyl)methylidene]-(2-methylquinolin-5-yl)amine are obtained as a yellow oil. 2.25 ml (26 mmol) 1,1,1-Trifluoroepoxypropane in 38 ml THF and 11 ml hexane are cooled to −100° C. and 15 ml of a 1.6 M n-butyl lithium solution in hexane are added over one hours while the temperature does not exceed −95° C. 10 Minutes after complete addition 3.6 g (11 mmol) raw [1-(2-methoxyphenyl)methylidene]-(2-methylquinolin-5-yl)amine in 49 ml THF are added over one hour while the temperature does not exceed −95° C. After one hour at −100° C. 12 ml diethyl ether are added and the reaction mixture is warmed to −10° C. over one hour. The reaction was quenched by addition of saturated ammonium chloride solution. The phases were separated and the aqueous layer was extracted twice with diethyl ether, the combined organic phases washed with brine, dried over sodium sulphate and then evaporated. Flash chromatography on silica gel (acetone in hexane 0 to 30%) yields 4.27 g {(2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methyl}-2-methylquinolin-5-amine as mixture of diastereomers.

後処理

  1. temperatureThe mixture is heated over 2 hours
  2. temperatureunder reflux
  3. filtrationfiltrated through a path of cellites
  4. temperatureafter cooling
  5. customThe solvent is evaporated

出典と根拠

ORDレコード
ord-9cdd4820327d4763a256e658895cd6f4
出典データセット
uspto-grants-2012_05
特許番号
US08173676B2

関連ノート

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