Quinoline, 1,2,3,4-tetrahydro-6-methoxy- → HCID 68194188, compound

HRID 1520138Notes

Reaction equation

HRID 1520138 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.[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH2:24][CH2:23][CH2:22]2>CN1C(=O)CCC1>[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]([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)[CH2:24][CH2:23][CH2:22]2

Participants

4

Reactant 2

HCID 67113Quinoline, 1,2,3,4-tetrahydro-6-methoxy-HCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 68194188HCID 68194188, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (700 mg, crude) in NMP (2 mL) was added 6-methoxy-1,2,3,4-tetrahydroquinoline (1.0 g, 6.13 mmol) with stifling for 3 h at 150° C. The reaction mixture was cooled to room temperature. The product was precipitated by the addition ethyl acetate and the solids were collected by filtration to afford methyl 3-(6-methoxy-1,2,3,4-tetrahydroquinolin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a light yellow solid (450 mg), which was used to the next step without further purification.

Workup

  1. customThe product was precipitated by the addition ethyl acetate
  2. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-65547aad8f0243ddbda9af6a5d6351ea
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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