1,3-Dichloro-2-nitrobenzene → 2-[4-(3-Chloro-2-nitroanilino)phenyl]ethanol

HRID 858425

反応式

HRID 858425 の反応式
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][CH:14]=1.C([O-])(=O)C.[Na+]>O>[Cl:8][C:4]1[C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 117591,3-Dichloro-2-nitrobenzeneHCID 669044-Aminophenethyl alcoholHCID 517045Sodium Acetate

生成物 1

HCID 218758492-[4-(3-Chloro-2-nitroanilino)phenyl]ethanol収率 72%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

A mixture of 2,6-dichloronitrobenzene (Norman, M. H.; Chen, N.; et al. PCT Int. Appl., WO 9940091 (1999)., Spada, A. P.; Fink, C. A.; Myers, M. R. PCT Int. Appl., WO 9205177 (1992)., 6.3 g, 32.8 mmol), 4-aminophenylethyl alcohol (4.9 g, 36 mmol) and sodium acetate (3.2 g, 39.3 mmol) was placed in a sealed tube and heated at 160° C. for 3 h. After cooling, the mixture was poured into water (100 mL) and extracted with ethyl acetate (300 mL). The organic layer was washed with 2N aqueous NaOH (100 mL) and brine (100 mL), then dried (Na2SO4), and concentrated. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to afford 4.57 g (72%) of the title compound as a red oil: 1H-NMR (CDCl3) δ 7.09–7.28 (6H, m), 6.91 (1H, dd, J=2.0, 7.1 Hz), 3.87 (2H, t, J=6.6 Hz), 2.86 (2H, t J=6.6 Hz).

後処理

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (300 mL)
  3. washThe organic layer was washed with 2N aqueous NaOH (100 mL) and brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-28c23d5b2037450aa8d02bb33d48c492
出典データセット
uspto-grants-2006_12
特許番号
US07148234B2

関連ノート

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