Diethyl Ether → {(2-Methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methyl}-2-methylquinolin-5-amine

HRID 1257497노트

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HRID 1257497 반응식
[F:1][C:2]([F:7])([F:6])[CH:3]1[O:5][CH2:4]1.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].COC1C=CC=CC=1C=[N:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27]([CH3:33])=[N:28]2.C(OCC)C.[CH2:39]1[CH2:43][O:42][CH2:41][CH2:40]1>CCCCCC>[CH3:41][O:42][C:43]1[CH:11]=[CH:10][CH:9]=[CH:8][C:39]=1[CH:40]([C:26]1[C:27]([CH3:33])=[N:28][C:29]2[CH:30]=[CH:31][CH:32]=[C:23]([NH2:22])[C:24]=2[CH:25]=1)[C:3]1([C:2]([F:7])([F:6])[F:1])[CH2:4][O:5]1

참가 물질

7

반응물 5

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2회HCID 5207692-(Trifluoromethyl)oxiraneHCID 67136395[1-(2-Methoxyphenyl)methylidene]-(2-methylquinolin-5-yl)amineHCID 178418339Butyllithium

생성물 1

HCID 86618227{(2-Methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methyl}-2-methylquinolin-5-amine

시약·촉매·용매 1

HCID 8058Hexane용매2회

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온도
-10 °C

실험 절차

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 diastereomeres.

후처리

  1. customdoes not exceed −95° C
  2. additionare added over one hour while the temperature
  3. customdoes not exceed −95° C
  4. customThe reaction was quenched by addition of saturated ammonium chloride solution
  5. customThe phases were separated
  6. extractionthe aqueous layer was extracted twice with diethyl ether
  7. washthe combined organic phases washed with brine
  8. dry with materialdried over sodium sulphate
  9. customevaporated

출처 및 근거

ORD 기록
ord-86256163ee474340a85982ccb71a7068
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461346B2

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