Methyl 4-aminobenzoate → HCID 178498133, 화합물

HRID 2045604노트

반응식

HRID 2045604 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH:5]=O.[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)/[CH:5]=[N:13]/[C:14]1[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=1

참가 물질

4

반응물 2

HCID 12082Methyl 4-aminobenzoateHCID 122489733-Chloro-5-nitrobenzaldehyde

생성물 1

HCID 178498133HCID 178498133, 화합물수율 1,085.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 3-chloro-5-nitrobenzaldehyde (371 mg, 0.1 mmol) in ethanol (6 mL) was added methyl 4-aminobenzoate (302 mg, 2.0 mmol). After a while, solids precipitated from the resulting clear yellow solution. The precipitated solid was filtered and 346 mg of (E)-methyl 4-(3-chloro-5-nitrobenzylideneamino)benzoate as a yellow solid was obtained. Yield=54%. 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. customAfter a while, solids precipitated from the resulting clear yellow solution
  2. filtrationThe precipitated solid was filtered

출처 및 근거

ORD 기록
ord-b20b540f78984a17b8692ec446cb2854
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586747B2

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