1,2,3,4-Tetrahydroquinoline → HCID 68194205, compound

HRID 1520149Notes

Reaction equation

HRID 1520149 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Cl[C:12]1[C:13](=[O:26])[NH:14][C:15]2[C:20]([N:21]=1)=[CH:19][C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=2>CN1C(=O)CCC1>[O:26]=[C:13]1[C:12]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)=[N:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=2)[NH:14]1

Participants

4

Reactant 2

HCID 694601,2,3,4-TetrahydroquinolineHCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 68194205HCID 68194205, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 1,2,3,4-tetrahydroquinoline (1.0 g, 7.51 mmol) in NMP (20 ml) was added methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (670 mg, 2.81 mmol) with stifling 3 h at 130° C. in an oil bath. The product was precipitated with water (80 ml), collected by filtration to afford methyl 2-oxo-3-(1,2,3,4-tetrahydroquinolin-1-yl)-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (700 mg, 28%).

Workup

  1. customThe product was precipitated with water (80 ml)
  2. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6c2d5f562cf34f6f86b8492a90fd0762
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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