5-Fluoro-1,2,3,4-tetrahydroquinoline → HCID 68194300, compound

HRID 1520171Notes

Reaction equation

HRID 1520171 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.[F:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH2:20][CH2:21][CH2:22][NH:23]2>CN1C(=O)CCC1>[F:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH2:20][CH2:21][CH2:22][N:23]2[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

Participants

4

Reactant 2

HCID 162443815-Fluoro-1,2,3,4-tetrahydroquinolineHCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 68194300HCID 68194300, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

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 5-fluoro-1,2,3,4-tetrahydroquinoline (1.5 g, 9.92 mmol) with stifling for 1 h at 150° C. in an oil bath. The reaction mixture was cooled 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-(5-fluoro-1,2,3,4-tetrahydroquinolin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a gray solid (1.0 g, crude).

Workup

  1. customprecipitated with water (100 mL)
  2. filtrationThe solids were collected by filtration
  3. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-8cc12799e8a04945bd85affc1900a5b9
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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