Reaction #2329003

Reaction equation

4-Aminoresorcinol hydrochloride

triethylamine

6-Methoxynicotinaldehyde

→

4-{[(6-methoxypyridin-3-yl)methylene]amino}benzene-1,3-diol

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe solvents were removed under reduced pressure
2. 2
   workup.ADDITIONthe mixture diluted with EtOAc
3. 3
   Washwashed with brine (2×)
4. 4
   Dryingdried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   Otherto give 1.31 g as a dark solid
8. 8
   OtherThe crude product was taken to the next step without further purification

Procedure

4-Aminoresorcinol hydrochloride (3.09 mmol) and triethylamine (3.25 mmol) were dissolved in dry methanol (20 mL). 6-Methoxynicotinaldehyde (3.09) was added and the mixture was stirred overnight. The solvents were removed under reduced pressure, the mixture diluted with EtOAc, washed with brine (2×), dried (Na2SO4), filtered and evaporated to give 1.31 g as a dark solid. The crude product was taken to the next step without further purification. MS m/z (M+H) 245.

Source