N,N-Dimethylaniline → Methyl 3-chloro-7-methoxy-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403588Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([NH:7][C:8](=O)[C:9](=[O:22])[N:10]2[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][C:4]=1[C:24]([O:26][CH3:27])=[O:25].O=P(Cl)(Cl)[Cl:30].CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:30][C:8]1[C:9](=[O:22])[N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:11]2[C:6]([N:7]=1)=[CH:5][C:4]([C:24]([O:26][CH3:27])=[O:25])=[C:3]([O:2][CH3:1])[CH:12]=2

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of methyl 7-methoxy-1-[(4-methoxyphenyl)methyl]-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate (24 g, 64.80 mmol) in toluene (300 mL) was added POCl3 (14.8 g, 96.52 mmol) and N,N-dimethylaniline (15.7 g, 129.75 mmol). The resulting solution was stirred overnight at 110° C. and concentrated in vacuo. The product was precipitated by the addition of methanol (150 mL) and collected by filtration to afford methyl 3-chloro-7-methoxy-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a green solid (17 g, 65%).

Workup

concentrationconcentrated in vacuo
customThe product was precipitated by the addition of methanol (150 mL)
filtrationcollected by filtration

Sources & evidence

ORD record: ord-a783d4f558ea4454ace8827c612a0487
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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