HCID 178498133, 화합물 → Methyl 2-(3-chloro-5-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 1801326노트

반응식

HRID 1801326 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1)/[CH:5]=[N:6]/[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1>O1CCCC1.FC(F)(F)S([O-])(=O)=O.[Y+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:10]([CH3:15])([CH3:9])[CH:11]([OH:12])[C:8]3[C:7](=[CH:16][CH:15]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=3)[NH:6]2)[CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1

참가 물질

4

반응물 1

HCID 178498133HCID 178498133, 화합물

생성물 1

HCID 67442943Methyl 2-(3-chloro-5-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate수율 117.4%

시약·촉매·용매 2

HCID 2733939Yttrium trifluoromethanesulfonate촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of (E)-methyl 4-(3-chloro-5-nitrobenzylideneamino)benzoate (346 mg, 1.09 mmol) in dry tetrahydrofuran (4 mL) was added yttrium(III) trifluoromethanesulfonate (34 mg, 0.054 mmol). The mixture was stirred under a nitrogen atmosphere. Then a solution of isobutyl aldehyde (95 mg, 1.30 mmol) in tetrahydrofuran (1 mL) was added via syringe. The mixture was stirred overnight. The reaction mixture was purified by column chromatography (petroleum ether: ethyl acetate=10:1) to afford 250 mg of methyl 2-(3-chloro-5-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a crude product. (Yield=59%). MS (ESI+APCI) M+1-water=373.

후처리

  1. stirringThe mixture was stirred overnight
  2. customThe reaction mixture was purified by column chromatography (petroleum ether: ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-7f0d715f85934be3a18121960d0cd8af
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344137B2

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