Ethyl Acetate → N-(2,4-dimethoxybenzyl)-6-methoxyquinoxalin-2-amine

HRID 250037Notes

Reaction equation

HRID 250037 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[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].C(OCC)(=O)C>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][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5972502,4-DimethoxybenzylamineHCID 126864122-Chloro-6-methoxyquinoxaline

Product 1

HCID 57476556N-(2,4-dimethoxybenzyl)-6-methoxyquinoxalin-2-amineYield 94.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Chloro-6-methoxyquinoxaline (0.93 g, 4.77 mmol) and (2,4-dimethoxyphenyl)methanamine (2.2 ml, 14.64 mmol) were microwaved in dimethylsulfoxide (5 mL) for 30 min at 150° C. The reaction was diluted into ethyl acetate (250 mL) and extracted with brine (3×100 mL). The crude product was purified by column chromatography (20 to 80% ethyl acetate/hexanes) to afford N-(2,4-dimethoxybenzyl)-6-methoxyquinoxalin-2-amine (1.46 g, 87% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.13 (1 H, s), 7.59-7.63 (1 H, m), 7.30 (1 H, d, J=8.31 Hz), 7.21-7.24 (2 H, m), 6.47 (1 H, d, J=2.27 Hz), 6.42 (1 H, dd, J=8.31, 2.27 Hz), 5.10 (1 H, t, J=5.92 Hz), 4.61 (2 H, d, J=5.79 Hz), 3.88 (3 H, s), 3.84 (3 H, s), 3.78 (3H, s). MS (LC/MS) R.T.=1.95; [M+H]+=326.23.

Workup

  1. extractionextracted with brine (3×100 mL)
  2. customThe crude product was purified by column chromatography (20 to 80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-71ff177f30b04a63abe78681707e7b93
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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