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

HRID 1912192Notes

Reaction equation

HRID 1912192 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-8fc277c09d364f28864c8c90a12804a2
Source dataset
uspto-grants-2013_12
Patent number
US08604042B2

Reaction notes

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