Toluene → 2-Methylindolizine-3-carbonyl chloride

Reaction equation

[C:1]([Cl:4])(Cl)=[O:2].C[C:6]1[CH:7]=[CH:8][N:9]2[C:14]=1[CH:13]=[CH:12][CH:11]=[CH:10]2.[C:15]1(C)C=CC=CC=1>>[CH3:15][C:7]1[CH:6]=[C:14]2[N:9]([C:8]=1[C:1]([Cl:4])=[O:2])[CH:10]=[CH:11][CH:12]=[CH:13]2

Participants

Reactant 3

HCID 1140Toluene2×

HCID 6371Phosgene

HCID 582636HCID 582636, compound

Product 1

HCID 203401302-Methylindolizine-3-carbonyl chloride

Procedure

A solution of 99 g of phosgene (1 mole) in 800 ml of anhydrous toluene was cooled beneath 15° C. While the reaction mixture was cooled and stirred a solution of 131 g of methylindolizine (1 mole) in 475 ml of anhydrous toluene was added dropwise. The reaction mixture was kept overnight and the residue formed was sucked off.