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

HRID 724066

반응식

HRID 724066 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
160 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f6957c13e555420f9102a4329d09369e
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141580B2

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