Hydrochloric Acid → HCID 9993627, compound
Reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[NH:11][C:12]([C:14]1[C:23]2[C:18](=[CH:19][C:20]([OH:24])=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:13].Cl.N1C=CC=CC=1.Cl>>[OH:24][C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[C:14]([C:12]1[O:13][C:3]3[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=3[N:11]=1)=[CH:15][CH:16]=[CH:17]2Participants
4
Conditions
- Temperature
- 200 °C
Procedure
A mixture of N-(2,5-dimethoxyphenyl)-6-hydroxy-1-naphthamide (2.0 g, 6.2 mmol), and pyridine hydrochloride (4.0 g, 34.6 mmol) was heated at 200° C. for 1 h. The reaction mixture was cooled to room temperature, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 1/1) gave a tan solid (1.45 g, 85% yield, m.p. 232-234° C.); MS m/e 278 (M+H)+.