Reaction #4116

Reaction equation

2-(5-methyl-7-nitroindolin-1-yl)benzoic acid

→

product

Yield 66.6%

4-Methyl-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one

Yield 66.6%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe solvent was removed
2. 2
   Washeluted with dichloromethane (4 l) and 2% methanol in dichloromethane (4 l)
3. 3
   workup.ADDITIONThe fractions containing product
4. 4
   Otherevaporated

Procedure

To a solution of 2-(5-methyl-7-nitroindolin-1-yl)benzoic acid (9 g, 0.03 mole), conc. hydrochloric acid (several drops) and ethanol (200 ml) was added 5% palladium-charcoal (1.5 gm). The mixture was shaked under hydrogen (58 psi) for 30 hours. The solvent was removed and the residue was loaded onto a silica gel flash chromatography column (800 g, 230-400 mesh), packed and eluted with dichloromethane (4 l) and 2% methanol in dichloromethane (4 l). The fractions containing product were pooled and evaporated to yield 5 g (66%) of product. Recrystallization from chloroform gave the analytical sample, mp 222°-224° C.

Source