Hydroquinone → 2-(2-chloro-5-methoxy-4-nitrophenyl)-N-(4-(4-methylpiperazin-1-yl)benzyl)ethanamine

HRID 1019764노트

반응식

HRID 1019764 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH:13]=[CH2:14].[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.C1(C=CC(O)=CC=1)O.O>C(O)CCC>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13][CH2:14][NH:27][CH2:26][C:25]1[CH:24]=[CH:23][C:22]([N:19]2[CH2:18][CH2:17][N:16]([CH3:15])[CH2:21][CH2:20]2)=[CH:29][CH:28]=1

참가 물질

6

반응물 4

HCID 785HydroquinoneHCID 962WaterHCID 2776493[4-(4-Methylpiperazin-1-yl)phenyl]methanamineHCID 674659471-Chloro-4-methoxy-5-nitro-2-vinylbenzene

생성물 1

HCID 674659782-(2-chloro-5-methoxy-4-nitrophenyl)-N-(4-(4-methylpiperazin-1-yl)benzyl)ethanamine수율 43%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A mixture of 1-chloro-4-methoxy-5-nitro-2-vinylbenzene (0.42 g, 1.95 mmol), 4-(4-methyl-piperazin-1-yl)-benzylamine (1.2 g, 5.85 mmol) and quinol (0.043 g, 0.39 mmol) in n-butanol (8 mL) was heated to reflux for 12 hours under a N2 atmosphere. Water (100 mL) was added and the reaction mixture extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 3-5% methanol in DCM to give the title compound (0.35 g, 43%) as a solid.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours under a N2 atmosphere
  3. extractionthe reaction mixture extracted with EtOAc (3×100 mL)
  4. washThe combined organic extracts were washed with brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on neutral silica gel using 3-5% methanol in DCM

출처 및 근거

ORD 기록
ord-5e344b53b38647c18371b876261e3489
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716287B2

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