Oxalyl chloride → Pyrrolo[3,2,1-ij]quinoline-1,2-dione
Reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH2:2]1.[C:11](Cl)(=[O:15])[C:12](Cl)=[O:13]>>[C:11]1(=[O:15])[C:9]2=[C:10]3[C:5](=[CH:6][CH:7]=[CH:8]2)[CH:4]=[CH:3][CH2:2][N:1]3[C:12]1=[O:13]Participants
3
Procedure
Generally speaking, the reaction of a 1,2-dihydroquinoline (II) with oxalyl chloride (III) to give a 4-H-pyrrolo[3,2,1-ij]quinolin-1,2-dione (I) is carried out in a dry aprotic solvent by the dropwise addition of a solution of the 1,2-dihydroquinoline in the same solvent to the stirred solution of oxalyl chloride in an inert atmosphere at or near room temperature. Subsequent to the addition the reaction mixture is briefly stirred at ambient temperature and then at gentle reflux to complete the reaction. The solvent is stripped from the reaction mixture at reduced pressure to give a solid residue which on crystallization from a selected solvent or solvent system furnishes the 4-pyrrolo[3,2,1-ij]quinoline-1,2-dione I.
Sources & evidence
- ORD record
- ord-644488113e584a4990e5d7683bc7e3ab