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

HRID 350437ノート

反応式

HRID 350437 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
110 °C

実験手順

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) δ 3.49 (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).

後処理

  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)]

出典と根拠

ORDレコード
ord-7896521b14b24dcb98f5407f5e44ce06
出典データセット
uspto-grants-2007_02
特許番号
US07179819B2

反応ノート

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