Reacción #479586

Ecuación de reacción

sodium borohydride

4-aminophenol

3-pyridinecarboxaldehyde

→

N-(4-hydroxyphenyl)pyridin-3-ylmethylamine

Disolventes

methanol ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe cooling bath was removed
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITcontinued for 20 hours
4. 4
   ConcentraciónThe reaction mixture was concentrated in vacuo
5. 5
   workup.ADDITIONThe residue was mixed with 1M HCl
6. 6
   Temperaturawarmed
7. 7
   Otropartitioned between ethyl acetate and 0.1M K2CO3
8. 8
   Extracciónthe product extracted 4-6 times with ethyl acetate
9. 9
   Lavadowashed with brine
10. 10
    Secadodried over anhydrous MgSO4
11. 11
    Concentraciónconcentrated

Procedimiento

Alternately, a solution of 4-aminophenol (1.0 equiv.) (Aldrich) in 2:1 methanol/ethanol was treated with 3-pyridinecarboxaldehyde (1.05 equiv.). The solution was allowed to stir for 1 hour. The reaction was cooled to 0° C. and treated with sodium borohydride (4.2 equiv.) in 5 portions. The cooling bath was removed and stirring continued for 20 hours. The reaction mixture was concentrated in vacuo. The residue was mixed with 1M HCl, warmed, and partitioned between ethyl acetate and 0.1M K2CO3. The pH of the aqueous phase was adjusted to pH=7 (using 1M HCl and 1M K2CO3) and the product extracted 4-6 times with ethyl acetate. The organic phases were combined, washed with brine, dried over anhydrous MgSO4, and concentrated to afford N-(4-hydroxyphenyl)pyridin-3-ylmethylamine. 1H NMR(400 MHz, DMSO-d6): d 4.18(2H, s), 5.65(1H, s), 6.41-6.53(4H, m), 7.29-7.32(1H, m), 7.70-7.72(1H, m), 8.39-8.40(2H, m), 8.53-8.54(1H, m). MS Found 201.2 [M+H]+.

Fuente