Ethyl Acetate → N-(2,4-dimethoxybenzyl)-7-methoxyquinoxalin-2-amine

HRID 250061Notes

Reaction equation

HRID 250061 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[CH2:24][NH2:25].CCOC(C)=O>CS(C)=O>[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[CH2:24][NH:25][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5972502,4-DimethoxybenzylamineHCID 126864152-Chloro-7-methoxyquinoxaline

Product 1

HCID 57476568N-(2,4-dimethoxybenzyl)-7-methoxyquinoxalin-2-amineYield 93.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Chloro-7-methoxyquinoxaline (0.51 g, 2.62 mmol), prepared according to J. Chem. Soc. Perk Trans. 1, 2001, 978-984, and (2,4-dimethoxyphenyl)methanamine (1.181 mL, 7.86 mmol) were microwaved in DMSO (2.5 mL) for 30 min at 150° C. This was diluted into 150 mL EtOAc and extracted three times with 100 mL brine. The crude product was purified by flash chromatography on a 90 g silica gel cartridge with 20 to 80% EtOAc in hexane, 50 min, at 40 mL/min to afford N-(2,4-dimethoxybenzyl)-7-methoxyquinoxalin-2-amine (795 mg, 2.443 mmol, 93% yield).

Workup

  1. extractionextracted three times with 100 mL brine
  2. customThe crude product was purified by flash chromatography on a 90 g silica gel cartridge with 20 to 80% EtOAc in hexane, 50 min, at 40 mL/min

Sources & evidence

ORD record
ord-e10112567dc647fb8bbae080d6ba792c
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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