1,2,3,4-Tetrahydroquinoline-6-carbonitrile → HCID 68194217, compound

HRID 1520154Notes

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.[NH:17]1[C:26]2[C:21](=[CH:22][C:23]([C:27]#[N:28])=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1>CN1C(=O)CCC1.O>[C:27]([C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[N:17]([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)[CH2:18][CH2:19][CH2:20]2)#[N:28]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (300 mg, 1.26 mmol) in NMP (0.5 mL) was added 1,2,3,4-tetrahydroquinoline-6-carbonitrile (597 mg, 3.77 mmol) with stirring for 1 h at 150° C. in an oil bath. The resulting solution was diluted with water (100 mL) and the solids were collected by filtration to afford methyl 3-(6-cyano-1,2,3,4-tetrahydroquinolin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (200 mg, 44%).

Workup

filtrationthe solids were collected by filtration

Sources & evidence

ORD record: ord-3d87b97bacc549b888e72842244d615f
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073902B2

Reaction notes

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