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

HRID 75369

反応式

HRID 75369 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-85a071288376462483692b25078970b3
出典データセット
uspto-grants-2014_09
特許番号
US08835432B2

関連ノート

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