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

HRID 1801326ノート

反応式

HRID 1801326 の反応式
[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

参加物

4

反応物 1

HCID 178498133HCID 178498133、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 2733939Yttrium trifluoromethanesulfonate触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-7f0d715f85934be3a18121960d0cd8af
出典データセット
uspto-grants-2013_01
特許番号
US08344137B2

反応ノート

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