7-Methoxy-1,2,3,4-tetrahydroquinoline → Methyl 3-(7-methoxy-1,2,3,4-tetrahydroquinolin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1520179Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][NH:10]2)=[CH:5][CH:4]=1.Cl[C:14]1[C:15](=[O:28])[NH:16][C:17]2[C:22]([N:23]=1)=[CH:21][C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=2>CN1C(=O)CCC1.O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][N:10]2[C:14]2[C:15](=[O:28])[NH:16][C:17]3[C:22]([N:23]=2)=[CH:21][C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=3)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 7-methoxy-1,2,3,4-tetrahydroquinoline (1.34 g, 8.21 mmol) in NMP (5 ml) was added methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (1.1 g, 4.61 mmol). The resulting solution was stirred for 1 h at 150° C. in an oil bath and then diluted with water (300 ml). The solids were collected by filtration to afford methyl 3-(7-methoxy-1,2,3,4-tetrahydroquinolin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a red solid (844 mg, 28%).

Workup

filtrationThe solids were collected by filtration

Sources & evidence

ORD record: ord-030dd0019f404e81b52d236c8835c6c2
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073902B2

Reaction notes

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