Water → 2-((3-Chloro-2-nitrophenyl)amino)butanoic acid

HRID 1019805

반응식

HRID 1019805 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][CH:13]([CH2:17][CH3:18])[C:14]([OH:16])=[O:15].C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([NH:12][CH:13]([CH2:17][CH3:18])[C:14]([OH:16])=[O:15])[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6657Alpha-Aminobutyric AcidHCID 11430Potassium CarbonateHCID 30175001-Chloro-3-fluoro-2-nitrobenzene

생성물 1

HCID 866985082-((3-Chloro-2-nitrophenyl)amino)butanoic acid수율 96.7%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
80 °C

실험 절차

A mixture of 1-chloro-3-fluoro-2-nitrobenzene (2.00 Kg, 11.4 mol), 2-aminobutyric acid (1.22 kg, 11.8 mol) and K2CO3 (1.58 Kg, 11.4 mol) in anhydrous DMSO (4.2 L) was heated at 80° C. for 16 h (after the reaction initiated, the internal temperature went up to 110° C.). At this time LC-MS analysis showed that the reaction was complete. After cooling to rt, the reaction mixture was carefully poured into water (10 L) with vigorous stirring. The aq. layer was washed with methyl tert-butyl ether (2×5 L) to remove organic impurities. The aq. layer was then acidified to pH ˜1.5 with cond HCl to give an orange solid. The orange solid was collected by filtration, washed with water (2×4 L) and air-dried to give 2-((3-chloro-2-nitrophenyl)amino)butanoic acid (2.85 Kg), which was used as such in the next step. 1H NMR (DMSO-d6) δ ppm 7.35 (t, J=8.3 Hz, 1H), 6.82-6.91 (m, 2H), 6.25 (d, J=7.6 Hz, 1H), 4.14 (td, J=7.4, 5.4 Hz, 1H), 3.4 (br. s., 1H), 1.74-1.92 (m, 2H), 0.88 (t, J=7.4 Hz, 3H). Mass Spectrum (ESI) m/z=259.2 (M+1).

후처리

  1. customwent up to 110° C.
  2. temperatureAfter cooling to rt
  3. washThe aq. layer was washed with methyl tert-butyl ether (2×5 L)
  4. customto remove organic impurities
  5. customto give an orange solid
  6. filtrationThe orange solid was collected by filtration
  7. washwashed with water (2×4 L)
  8. customair-dried

출처 및 근거

ORD 기록
ord-fd0fc93124c14b7698764fc88c16bdf6
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716290B2

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