HCID 18998824, compound → HCID 68194088, compound

HRID 1520188Notes

Reaction equation

HRID 1520188 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.[O:17]1[C:21]2=[CH:22][C:23]3[CH2:24][CH2:25][CH2:26][NH:27][C:28]=3[CH:29]=[C:20]2[O:19][CH2:18]1>CN1C(=O)CCC1>[O:17]1[C:21]2=[CH:22][C:23]3[CH2:24][CH2:25][CH2:26][N:27]([C:2]4[C:3](=[O:16])[NH:4][C:5]5[C:10]([N:11]=4)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=5)[C:28]=3[CH:29]=[C:20]2[O:19][CH2:18]1

Participants

4

Reactant 2

HCID 18998824HCID 18998824, compoundHCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 68194088HCID 68194088, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (161 mg, 0.67 mmol) in NMP (5 ml) was added the 2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]quinoline (180 mg, 1.02 mmol) and the reaction was stirred for 1 h at 140° C. The reaction mixture was cooled to room temperature, and the product was precipitated by the addition of water and filtered off to afford methyl 3-[2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]quinolin-5-yl]-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a brown solid (140 mg, 55%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe product was precipitated by the addition of water
  3. filtrationfiltered off

Sources & evidence

ORD record
ord-2b8ec1f38f7743d69acb3710baa2b853
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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