Reacción #417941

Ecuación de reacción

NaHCO3

methyl 3-amino-4-hydroxybenzoate

methyl 4-formylbenzoate

DDQ

→

compound 1

Rendimiento 86.0%

3,4-diamino-benzoic acid ethyl ester

Rendimiento 86.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated under reduced pressure
2. 2
   workup.DISSOLUTIONthe remaining residue was dissolved in dichloromethane (150 mL)
3. 3
   workup.STIRRINGthe reaction mixture was stirred at rt for 1 h
4. 4
   FiltraciónThe suspension was filtered off
5. 5
   Lavadothe resulting solid was washed with saturated NaHCO3 (50 mL), water (50 mL), and ethyl acetate (100 mL)
6. 6
   Otrodried in vacuo

Procedimiento

A mixture of methyl 3-amino-4-hydroxybenzoate (2.5 g, 15 mmol) and methyl 4-formylbenzoate (2.46 g, 15 mmol) in methanol (75 mL) was stirred at rt overnight. The solvent was evaporated under reduced pressure and the remaining residue was dissolved in dichloromethane (150 mL). DDQ (3.5 g, 15.4 mmol) was added and the reaction mixture was stirred at rt for 1 h. Saturated NaHCO3 (200 mL) was added. The suspension was filtered off, the resulting solid was washed with saturated NaHCO3 (50 mL), water (50 mL), and ethyl acetate (100 mL) and dried in vacuo to give compound 1 (4 g, 86% yield) as yellow solid.

Fuente