Naphthalene → HCID 18001048, compound

HRID 441233Notes

Reaction equation

HRID 441233 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

5

Reactant 3

HCID 931NaphthaleneHCID 5360545SodiumHCID 22405061HCID 22405061, compound

Product 1

HCID 18001048HCID 18001048, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

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).

Workup

  1. stirringthe solution was stirred at the same temperature for 30 minutes
  2. customThe reaction mixture was quenched with water
  3. extractionthe solution was extracted with chloroform
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customto give an oil
  8. customthe crude oil was purified by silica gel column

Sources & evidence

ORD record
ord-97057135d9fd449496cc24f86fdf4047
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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