반응 #509374

반응 방정식

7-hydroxy-1-tetralone

6-chloronicotinamide

K2CO3

DMA

→

title compound

5-(8-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-nicotinamide

용매

toluene

반응 조건

후처리

1. 1
   온도Reflux the suspension for 2-3 hours
2. 2
   기타Remove the solids
3. 3
   여과via filtration
4. 4
   세척wash solids with EtOAc
5. 5
   농축concentrate the
6. 6
   세척filtrate/wash on a rotary evaporator
7. 7
   workup.DISSOLUTIONDissolve the remaining oil in EtOAc
8. 8
   세척wash with water (2×) and brine
9. 9
   건조dry (MgSO4)
10. 10
    농축concentrate
11. 11
    기타Triturate the resulting brown solid with boiling EtOAc
12. 12
    온도cool
13. 13
    기타collect solid
14. 14
    여과via filtration

실험 절차

Combine 7-hydroxy-1-tetralone (J. Med. Chem. (1998), 41(7), 1068-1083), (3.37 g, 20.7 mmol), 6-chloronicotinamide (available from Aldrich Chemical Company, Milwaukee, USA) (2.95 g, 18.8 mmol, K2CO3 (3.91 g, 28.3 mmol), DMA (dimethylacetamide) (45 ml) and toluene (25 ml) in a round bottom flask, equipped with Dean-Stark trap, condenser, and nitrogen inlet. Reflux the suspension for 2-3 hours before cooling to ambient temperature. Remove the solids via filtration, wash solids with EtOAc, and concentrate the filtrate/wash on a rotary evaporator. Dissolve the remaining oil in EtOAc, wash with water (2×) and brine, dry (MgSO4) and concentrate. Triturate the resulting brown solid with boiling EtOAc, cool, and collect solid via filtration to give 4.76 g of the title compound as a yellow solid. Mass Spectrum (ion spray): m/z=283 (M+1); 1HNMR (DMSO-d6): 8.56 (s, 1H), 8.25 (d, 1H), 8.02 (s, 1H), 7.52 (s, 1H), 7.48 (s, 1H), 7.42 (d, 1H), 7.35 (d, 1H), 7.12 (d, 1H), 2.95 (t, 2H), 2.60 (t, 2H), 2.05 (m, 2H).

출처