Reaktion #46718

Reaktionsgleichung

NaOH

4-amino salicylic acid

sodium triacetoxyborohydride

3-nitrobenzaldehyde

→

yellowish powder

Ausbeute 55.5%

2-Hydroxy-4-(3-nitro-benzylamino)-benzoic acid

Ausbeute 55.5%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigethe two layers separated
3. 3
   Sonstigethe precipitate formed
4. 4
   Filtrationfiltered off
5. 5
   Sonstigedried

Vorschrift

To a solution of 4-amino salicylic acid (153 mg; 1 mmol) in 1,2-dichloroethane (4 mL) under argon atmosphere was added sodium triacetoxyborohydride (317 mg; 1.5 mmol) and 3-nitrobenzaldehyde (226 mg; 1.5 mmol). The mixture was stirred at room temperature under argon overnight after which time 1 M NaOH (sq.; 5 mL) was added and the two layers separated. The aqueous layer was acidified with 2 M HCl (aq) and the precipitate formed filtered off and dried to yield 160 mg (55%) of a yellowish powder with satisfactorily purity. Mp. 189° C. (decomposes); MS (ESI−): 287 (MH−).

Quelle