Reaction #1509590

Reaction equation

methylamine

3-chlorocarbonyl-5-nitro-benzoic acid ethyl ester

→

title compound

N-Methyl-5-nitro-isophthalamic acid ethyl ester

Solvents

THF

THF

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   ConcentrationThe filtrate was concentrated in vacuum
3. 3
   Otherthe solid recrystallised from diethyl ether

Procedure

To a 2M solution of methylamine in THF (256 ml) at −20° C. was added a pre-cooled solution of 3-chlorocarbonyl-5-nitro-benzoic acid ethyl ester (60 g) in THF (500 ml) dropwise. This was stirred for 20 min and then filtered. The filtrate was concentrated in vacuum and the solid recrystallised from diethyl ether to give the title compound (22.5 g) as a solid. An oxalyl chloride solution in DCM (63 ml, 2M), was added with DMF (5 ml). The reaction was stirred for 2 h and then concentrated in vacuum. The residue was triturated with toluene and again concentrated in vacuum leaving the title compound (60 g). Rt=1.53 min (method D).

Source