Acetic Acid → Methyl 2-(4-amino-3-chlorophenyl)acetate

HRID 354373노트

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HRID 354373 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C(O[Na])(C)=O.O.O.O.CC(O)=O>CO.O>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:3][C:2]=1[Cl:1]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 10376538Methyl 3-chloro-4-nitrophenylacetateHCID 178476686sodium;acetate;trihydrate

생성물 1

HCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate수율 48.3%

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

반응 조건

온도
110 °C

실험 절차

A mixture of methyl 3-chloro-4-nitrophenylacetate (10.9 g, 47.5 mmol), reduced iron powder (8.58 g, 153.6 mmol), AcONa.3H2O (6.05 g, 44.5 mmol) and AcOH (17.6 ml) in MeOH/H2O (100/400 ml) was heated at 110° C. for 1 h. After cooled to room temperature, the reaction mixture was filtered through Celite and the filtered cake was washed with MeOH. The combined filtrate were evaporated and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel [150 g, CHCl3/EtOAc (10/1)] to give methyl 4-amino-3-chlorophenylacetate (4.58 g, 48%) as a red oil. 1H-NMR (CDCl3) δ3.49 (s, 2H), 3.68 (s, 3H), 4.01 (br, 2H), 6.70 (d, J=7.4 Hz, 1H), 6.96 (dd, J=8.1, 2.0 Hz, 1H), 7.17 (d, J=2.0 Hz, 1H).

후처리

  1. temperatureAfter cooled to room temperature
  2. filtrationthe reaction mixture was filtered through Celite
  3. washthe filtered cake was washed with MeOH
  4. customThe combined filtrate were evaporated
  5. extractionextracted with EtOAc
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel [150 g, CHCl3/EtOAc (10/1)]

출처 및 근거

ORD 기록
ord-e0b182b591604aaf82f55538643297c4
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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