Reaktion #577998

Reaktionsgleichung

5-methyl-pyridine-3-carbaldehyde

4-hydroxy-1-methyl-indole

malononitrile

piperidine

→

2-Amino-3-cyano-4-(5-methyl-pyridin-3-yl)-7-methyl-4H-pyrrolo[2,3-h]chromene

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe product was collected by vacuum filtration
2. 2
   Waschenwashed with ethanol
3. 3
   Trocknendried in vacuo as a yellow powder (269 mg, 86%)

Vorschrift

To a solution of 5-methyl-pyridine-3-carbaldehyde (121 mg, 1 mmol) and 4-hydroxy-1-methyl-indole (146 mg, 0.99 mmol) in absolute ethanol (5 mL) at 0° C., was added malononitrile (67 mg, 1.01 mmol) and piperidine (0.1 mL). The clear solution was slowly warmed to room temperature and stirred overnight. The product was collected by vacuum filtration, washed with ethanol, and dried in vacuo as a yellow powder (269 mg, 86%). 1H NMR (CDCl3): 8.34 (d, J=2.1 Hz, 1H), 8.31 (dd, J=0.6, 2.1 Hz, 1H), 7.29 (m, 1H), 7.06 (d, J=3.0 Hz, 1H), 7.02 (dd, J=0.9, 8.4 Hz, 1H), 6.72 (d, J=8.4 Hz, 1H), 6.57 (dd, J=0.9, 3.0 Hz, 1H), 4.85 (s, 1H), 4.72 (brs, 2H), 3.77 (s, 3H), 2.27 (s, 3H).

Quelle