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

HRID 2420709노트

반응식

HRID 2420709 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-b65a6931642340a2b71d758625d8efd8
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956049B2

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