Ethyl Acetate → 3-Chloro-4-[2-(pyrrolidin-1-yl)ethoxy]aniline

HRID 2420709ノート

反応式

HRID 2420709 の反応式
[Cl:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.CCOC(C)=O>CC(O)=O.[Zn]>[Cl:1][C:2]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1

参加物

5

反応物 2

HCID 8857Ethyl AcetateHCID 574214731-[2-(2-chloro-4-nitrophenoxy)ethyl]Pyrrolidine

生成物 1

HCID 196269953-Chloro-4-[2-(pyrrolidin-1-yl)ethoxy]aniline

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

A suspension of Zn powder (620 mg, 9.48 mmol) and 1-(2-(2-chloro-4-nitrophenoxy)ethyl)pyrrolidine (320 mg, 1.19 mmol) in AcOH:H2O (3:1 mL) was heated, at 55° C. for 2 h. After cooling the reaction to RT, any solid was removed by filtration and rinsed with AcOH and CH2Cl2. Once the combined filtrate was concentrated using a rotavap, the resulting residue was adjusted pH to 10 with NH4OH and extracted with CH2Cl2 (2×50 mL). The combined organic layers were washed with H2O (10 mL), then dried over MgSO4. After removal of the solvent under vacuum the pale brownish oil (0.26 g, 93%) was carried forward without further purification. MS (ESI) 241 (M+H)+.

後処理

  1. temperatureAfter cooling
  2. customthe reaction to RT
  3. customany solid was removed by filtration
  4. washrinsed with AcOH and CH2Cl2
  5. concentrationOnce the combined filtrate was concentrated
  6. extractionextracted with CH2Cl2 (2×50 mL)
  7. washThe combined organic layers were washed with H2O (10 mL)
  8. dry with materialdried over MgSO4
  9. customAfter removal of the solvent under vacuum the pale brownish oil (0.26 g, 93%)
  10. customwas carried forward without further purification

出典と根拠

ORDレコード
ord-b65a6931642340a2b71d758625d8efd8
出典データセット
uspto-grants-2011_06
特許番号
US07956049B2

反応ノート

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