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Water → 5-Amino-2-(2-pyrrolidin-1-yl-ethoxy)-benzoic acid methyl ester

HRID 1095047
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HRID 1095047 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[OH:11].Cl.Cl[CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1
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참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 135127Methyl 5-amino-2-hydroxybenzoate

생성물 1

HCID 575164935-Amino-2-(2-pyrrolidin-1-yl-ethoxy)-benzoic acid methyl ester수율 13%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
60 °C

실험 절차

A suspension of 5-amino-2-hydroxy-benzoic acid methyl ester (1.0 g, 6.0 mmol), 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (1.2 g, 7.1 mmol) and cesium carbonate (5.0 g, 15 mmol) in DMF (40 mL) was heated at 60° C. for 17 h. The mixture was allowed to cool to room temperature, poured into water (60 mL) and extracted with EtOAc (2×50 mL). The combined extracts were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (DCM to 30% MeOH/DCM) to afford the title compound (0.2 g, 13%) as a light brown solid. MS (ES+): m/z 265 (M+H)+.

후처리

  1. temperatureto cool to room temperature
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue purified by flash chromatography on silica gel (DCM to 30% MeOH/DCM)

출처 및 근거

ORD 기록
ord-4d32ebcfd40f4b7db39c3701321d5b06
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08133900B2

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