반응 #51887

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3.5-Difluoro-4-[bis(2-hydroxyethyl) amino]benzonitrile

NaOH

ethanol

→

pure white crystals

수율 87.0%

3.5-difluoro-4-[bis(2-hydroxyethyl)amino]benzoic acid

수율 87.0%

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후처리

1. 1
   기타The solution was then partitioned between EtOAc (800 ml) and HCl (330 ml, 0.4 M)
2. 2
   세척the aqueous layer washed with EtOAc (3×150 ml)
3. 3
   건조the combined organic layers dried (MgSO4)
4. 4
   기타evaporated to dryness
5. 5
   기타The solid recrystallized from EtOAc (100 ml)

실험 절차

A solution of the 3.5-Difluoro-4-[bis(2-hydroxyethyl) amino]benzonitrile (3.15 g, 13 mmol) and NaOH (5.2 g, 0.13 mol) in aqueous ethanol (65 ml, 50%) was refluxed for 2.5 hours. The solution was then partitioned between EtOAc (800 ml) and HCl (330 ml, 0.4 M), the aqueous layer washed with EtOAc (3×150 ml), the combined organic layers dried (MgSO4) and evaporated to dryness. The solid recrystallized from EtOAc (100 ml) to give 2.94 g (87%) of pure white crystals: mp 146.5-150° C.; 1H NMR δ 3.3 (t, 4H, CH2N), 3.46 (q, 4H, CH2O, J=5.5 Hz), 4.49 (t, 2H, OH, J=5 Hz), 7.44 (d, 2H, H2+6, J=10.5 Hz), 13.1 (bs, 1H, CO2H); 19F NMR δ −117.3 (d, 2F, F3+5, J=9.5 Hz); MS m/z 284 (M+Na+, 15), 262 (M+H+, 100), 230 (M-CH2OH, 40). Anal. (C11H13NO4F2) C,H,N.

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