Reaktion #503805

Reaktionsgleichung

p-nitrobenzoyl chloride

3-amino-4-hydroxypyridine

Na2CO3

AcOH

→

N-(4-hydroxypyridin-3-yl)-4-nitrobenzamide

Ausbeute 62.0%

Lösungsmittel

pyridine

pyridine

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe precipitate was collected by filtration
2. 2
   Waschenwashed with 10% AcOH
3. 3
   Sonstigedried in vacuo (50° C.)

Vorschrift

A solution of p-nitrobenzoyl chloride (4.8 g, 25.7 mmol) in pyridine (77.0 mL) was added dropwise to a solution of 3-amino-4-hydroxypyridine (3.4 g, 30.9 mmol) in pyridine (51.0 mL) at 10° C. and stirred overnight. A solution of Na2CO3 (1.7 g) in water (65 mL) was added and the resultant mixture was stirred for 1 h. The reaction mixture was neutralized with 10% AcOH. The precipitate was collected by filtration, washed with 10% AcOH, and dried in vacuo (50° C.) to afford N-(4-hydroxypyridin-3-yl)-4-nitrobenzamide as a light green powder (4.1 g, Yield: 62%). 1HNMR (400 MHz, DMSO-d6) δ: 11.64 (1H, br s), 9.57 (1H, s), 9.07 (1H, s), 8.75 (1H, d, J=4.4 Hz), 8.36 (1H, d, J=8.8 Hz), 8.20 (1H, d, J=8.8 Hz), 7.74 (1H, d, J=4.4 Hz), 6.33 (1H, s); MS (ESI) calcd for C12H9N3O (m/z): 211. found: 212 [M+1]+.

Quelle