Reaction #792149

Reaction equation

isopropylamine

3-methyl-2-nitrobenzoic acid

triethylamine

Ethyl chloroformate

→

desired intermediate

Yield 80.2%

3-Methyl-N-(1-methylethyl)-2-nitrobenzamide

Yield 80.2%

Solvents

methylene chloride

water

Conditions

Workup

1. 1
   Othera solid precipitate formed
2. 2
   workup.ADDITIONwas added
3. 3
   Othera homogeneous solution resulted
4. 4
   Extractionextracted with ethyl acetate
5. 5
   WashThe organic extracts were washed with water
6. 6
   Dryingdried over magnesium sulfate
7. 7
   Otherevaporated under reduced pressure

Procedure

A solution of 3-methyl-2-nitrobenzoic acid (2.00 g, 11.0 mmol) and triethylamine (1.22 g, 12.1 mmol) in 25 mL of methylene chloride was cooled to 10° C. Ethyl chloroformate was carefully added and a solid precipitate formed. After stirring for 30 minutes isopropylamine (0.94 g, 16.0 mmol) was added and a homogeneous solution resulted. The reaction was stirred for an additional hour, poured into water and extracted with ethyl acetate. The organic extracts were washed with water, dried over magnesium sulfate and evaporated under reduced pressure to afford 1.96 g of the desired intermediate as a white solid melting at 126-128° C.

Source