6-Chloro-1,2,3,4-tetrahydroquinoline → Methyl 3-(6-chloro-1,2,3,4-tetrahydroquinolin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1520167Notes

Reaction equation

Cl[C:2]1[C:3](=[O:16])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH2:23][CH2:22][CH2:21]2>CN1C(=O)CCC1>[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]([C:2]1[C:3](=[O:16])[NH:4][C:5]3[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH2:23][CH2:22][CH2:21]2

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (1.0 g, 4.19 mmol) in NMP (10.0 ml) was added 6-chloro-1,2,3,4-tetrahydroquinoline (1.20 g, 7.16 mmol) and the reaction was stirred for 1 h at 150° C. in an oil bath. The reaction mixture was cooled down to room temperature, precipitated with water (100 ml). The solids were collected by filtration and dried in an oven under reduced pressure to afford methyl 3-(6-chloro-1,2,3,4-tetrahydroquinolin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a gray solid (1.0 g, crude).

Workup

temperatureThe reaction mixture was cooled down to room temperature
customprecipitated with water (100 ml)
filtrationThe solids were collected by filtration
customdried in an oven under reduced pressure

Sources & evidence

ORD record: ord-f8426fbe7652466684b7879c379ce9e1
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073902B2

Reaction notes

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