反応 #417941

反応方程式

NaHCO3

methyl 3-amino-4-hydroxybenzoate

methyl 4-formylbenzoate

DDQ

→

compound 1

収率 86.0%

3,4-diamino-benzoic acid ethyl ester

収率 86.0%

溶媒

methanol

反応条件

後処理

1. 1
   その他The 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
   ろ過The suspension was filtered off
5. 5
   洗浄the resulting solid was washed with saturated NaHCO3 (50 mL), water (50 mL), and ethyl acetate (100 mL)
6. 6
   その他dried in vacuo

実験手順

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.

出典