Reaction #6907

Reaction equation

2-iodoaniline

dimethylmaleate

triethylamine

→

methyl 2-oxo-1,2-dihydroquinoline-4-carboxylate

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherThe tube was flushed with nitrogen
2. 2
   Othersealed
3. 3
   TemperatureThe sealed tube was heated at 100° for 3.5 h
4. 4
   Filtrationthe resulting solids filtered
5. 5
   Washwashed with acetonitrile
6. 6
   workup.DISSOLUTIONThe solids were dissolved in chloroform
7. 7
   Otherthe solvent removed under vacuum
8. 8
   Otherto provide a solid

Procedure

In a heavy-walled PYREX tube was placed 2-iodoaniline (2.84 g, 13 mmol), dimethylmaleate (2.44 g, 17 mmol), triethylamine (1.4 mL, 10 mmol), palladium diacetate (31 mg, 0.14 mmol) and 6 mL acetonitrile. The tube was flushed with nitrogen and sealed. The sealed tube was heated at 100° for 3.5 h then cooled to r.t. The tube was opened and the resulting solids filtered and washed with acetonitrile. The solids were dissolved in chloroform and the solvent removed under vacuum to provide a solid.

Source