Reaction #57787

Reaction equation

NH4Cl

2-amino-5-chlorobenzoic acid

nBuLi

N-methyl imidazole

→

product

Yield 13.7%

(2-Amino-5-chloro-phenyl)-(1-methyl-1H-imidazol-2-yl)-methanone

Yield 13.7%

Solvents

ether

hexane

Conditions

Workup

1. 1
   Temperaturerefluxed for 1 h
2. 2
   workup.STIRRINGThe reaction mixture was stirred overnight at rt
3. 3
   Extractionthe resulting mixture extracted with ethyl acetate (2×150 ml)
4. 4
   DryingThe combined organic layers were dried over Na2SO4
5. 5
   OtherAfter removal of solvent
6. 6
   Otherthe residue was purified by the flash chromatography
7. 7
   OtherCrystallization of the product from Et2O/hexane mixture

Procedure

To a solution of nBuLi (0.0730 mol) in hexane was added N-methyl imidazole (0.0608 mol) drop wise at -40° C. over 30 min under a nitrogen atmosphere. The resulting yellow solution was stirred for a further 3 hr at rt, and then refluxed for 1 h. 2-amino-5-chlorobenzoic acid (1.74 g, 0.01014 mole) in dry ether (60 ml) was then added to the reaction mixture. The reaction mixture was stirred overnight at rt. To the reaction mixture was added saturated NH4Cl solution and the resulting mixture extracted with ethyl acetate (2×150 ml). The combined organic layers were dried over Na2SO4. After removal of solvent, the residue was purified by the flash chromatography using ethyl acetate/hexane (1:4) as eluent. Crystallization of the product from Et2O/hexane mixture gave 300 mg (13.7%) of product as yellow solid.

Source