반응 #417941

반응 방정식

NaHCO3

methyl 3-amino-4-hydroxybenzoate

methyl 4-formylbenzoate

DDQ

→

compound 1

수율 86.0%

3,4-diamino-benzoic acid ethyl ester

수율 86.0%

용매

methanol

반응 조건

후처리

1. 1
   기타The 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
   여과The suspension was filtered off
5. 5
   세척the resulting solid was washed with saturated NaHCO3 (50 mL), water (50 mL), and ethyl acetate (100 mL)
6. 6
   기타dried in vacuo

실험 절차

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.

출처