Réaction #487520

Équation de réaction

dimethylamine

6-methoxy-naphthaldehyde

phosphate

n-butyllithium

2-bromo-6-methoxynaphthalene

n-butyllithium

→

6-Methoxy-2-naphthaldehyde

6-dimethylamino-2-naphthaldehyde

Rendement 84.0%

Solvants

dimethylformamide

hexamethylphosphoramide

benzene

ether

Conditions de réaction

Traitement

1. 1
   Autre6-Dimethylamino-2-naphthaldehyde is prepared
2. 2
   workup.DISSOLUTIONis dissolved
3. 3
   workup.WAITis continued for 14 hours at 20° C.
4. 4
   Extractionis extracted with ether
5. 5
   AutrePurification by chromatography

Mode opératoire

6-Methoxy-2-naphthaldehyde is prepared by successive treatment of 2-bromo-6-methoxynaphthalene in solution in dry ether with n-butyllithium and then dimethylformamide. (Literature: J. Med. Chem. 1998, 1308-1312). 6-Dimethylamino-2-naphthaldehyde is prepared according to the described procedure (Barbas et al., Proc. Natl. Acad. Sci. USA 1998, 95, 15351) as follows: gaseous dimethylamine is introduced into a mixture of 2.4 ml of dry benzene and 2.4 ml of hexamethylphosphoramide (HMPA) until 750 mg (16.7 mmol) is dissolved. At 0° C. and under inert atmosphere, n-butyllithium (1.6 M in hexane, 16.7 mmol) is added, then after 15 minutes, 6-methoxy-naphthaldehyde (390 mg, 2.09 mmol) is added. Stirring is continued for 14 hours at 20° C., then it is poured into aqueous phosphate buffer, pH 7.4, and it is extracted with ether. Purification by chromatography provides 6-dimethylamino-2-naphthaldehyde (350 mg, 84%).

Source