Naphthalene → HCID 18001048, compound

Reaction equation

C1C2C(=CC=CC=2)C=CC=1.[Na].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[N:22](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:21][CH2:20][CH2:19][CH:18]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:17]=2[CH:39]=1>C(COC)OC>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[NH:22][CH2:21][CH2:20][CH2:19][CH:18]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:17]=2[CH:39]=1

Participants

Procedure

To a solution of naphthalene (15.5 g) in dimethoxyethane (100 ml) was added sodium metal (2.79 g) in portions at 0° C. and the solution was stirred at the same temperature for 1 hour. The naphthilide was added to a solution of 7-chloro -5-ethoxycarbonylmethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (9.89 g) in dimethoxyethane (400 ml) at -60° C. and the solution was stirred at the same temperature for 30 minutes. The reaction mixture was quenched with water and the solution was extracted with chloroform. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo to give an oil and the crude oil was purified by silica gel column to give 7-chloro-5-ethoxycarbonylmethyl -2,3,4,5-tetrahydro-1H-1-benzazepine (2.31 g).