1-Pyrrolidineethanamine → 4-Nitro-3-(2-pyrrolidin-1-yl-ethylamino)-benzoic acid methyl ester

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6](F)[CH:5]=1.[N:15]1([CH2:20][CH2:21][NH2:22])[CH2:19][CH2:18][CH2:17][CH2:16]1>CO.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([NH:22][CH2:21][CH2:20][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:5]=1

Participants

Procedure

3-Fluoro-4-nitro-benzoic acid methyl ester (xiv) (1.08 g, 5.41 mmol) and 2-pyrrolidin-1-yl-ethylamine (1.36 g, 11.9 mmol) in MeOH (19 mL) were stirred under microwave irradiation at 100° C. for 10 min. The RM was diluted with EtOAc and washed with aqueous saturated NaHCO3 and brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was dry loaded on silica gel and purified by chromatography with DCM and MeOH to yield the title product as an orange solid (tR 2.45 min (conditions 8), MH+=294).