4-Methoxybenzylamine → 3-(4-Methoxybenzylamino)-5-chloro-6-methyl-1-carboxymethylpyrazinone

HRID 361376Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.Cl[C:12]1[C:13](=[O:24])[N:14]([CH2:20][C:21]([OH:23])=[O:22])[C:15]([CH3:19])=[C:16]([Cl:18])[N:17]=1>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:12]2[C:13](=[O:24])[N:14]([CH2:20][C:21]([OH:23])=[O:22])[C:15]([CH3:19])=[C:16]([Cl:18])[N:17]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4-Methoxybenzylamine (0.83 ml, 6.33 mmol) was added to a stirred solution of 3,5-dichloro-6-methyl-1-carboxymethylpyrazinone (0.50 g, 2.11 mmol) in dioxane (6 ml) and the resulting mixture was warmed to 60° C. After 16 h the reaction mixture was partitioned between chloroform and 10% citric acid solution and the organic layer was dried (Na2SO4) and evaporated in vacuo. The crude product was purified by flash column chromatography (eluting with 2% methanol/chloroform/2% acetic acid) to give after azeotroping dry with toluene/methanol the title compound as a white solid:

Workup

customAfter 16 h the reaction mixture was partitioned between chloroform and 10% citric acid solution
dry with materialthe organic layer was dried (Na2SO4)
customevaporated in vacuo
customThe crude product was purified by flash column chromatography (eluting with 2% methanol/chloroform/2% acetic acid)
customto give
customafter azeotroping
dry with materialdry with toluene/methanol the title compound as a white solid

Sources & evidence

ORD record: ord-cf79c3c6e82c478490e48655b3b64635
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866573

Reaction notes

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