Реакция #417941

Уравнение реакции

NaHCO3

methyl 3-amino-4-hydroxybenzoate

methyl 4-formylbenzoate

DDQ

→

compound 1

Выход 86.0%

3,4-diamino-benzoic acid ethyl ester

Выход 86.0%

Растворители

methanol

Условия реакции

Обработка

1. 1
   ДругоеThe 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
   ФильтрацияThe suspension was filtered off
5. 5
   Промывкаthe resulting solid was washed with saturated NaHCO3 (50 mL), water (50 mL), and ethyl acetate (100 mL)
6. 6
   Другоеdried in vacuo

Методика

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.

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