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

HRID 1019764ノート

反応式

HRID 1019764 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5e344b53b38647c18371b876261e3489
出典データセット
uspto-grants-2014_05
特許番号
US08716287B2

反応ノート

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