Reaction #1605772

Reaction equation

NH3

2-methoxy-4-methylbenzoic acid

EDC

HOBt

→

2-methoxy-4-methylbenzamide

Yield 83.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Washthen washed successively with HCl (1N)
2. 2
   DryingNaHCO3, water and brine, dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated
5. 5
   OtherThe residue was recrystallized from ethyl acetate/hexane

Procedure

To a mixture of 2-methoxy-4-methylbenzoic acid (20 g, 120.4 mmol), EDC (23.1 g, 120.4 mmol) and HOBt (16.3 g, 120.4 mmol) in dichloromethane (1 L) was added NH3 (7N in MeOH, 52 mL, 3 eq) dropwise. The reaction mixture was stirred at room temperature overnight then washed successively with HCl (1N), saturated aq.NaHCO3, water and brine, dried over MgSO4, filtered and evaporated. The residue was recrystallized from ethyl acetate/hexane to give 16.5 gr of 2-methoxy-4-methylbenzamide (83% yield).

Source