Benzoyl chloride → N-[2-(7-methoxy-3-benzoylnaphth-1-yl)ethyl]acetamide

HRID 232780Notes

Reaction equation

HRID 232780 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>[N+](C1C=CC=CC=1)([O-])=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:9]=[C:10]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 82148AgomelatineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15289276N-[2-(7-methoxy-3-benzoylnaphth-1-yl)ethyl]acetamide

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

To a solution of 11 g (45.2 mmol) of N-[2-(7-methoxynaphth-1-yl)ethyl]acetamide and 7.7 g (57.7 mmol) of AlCl3 in 60 cm3 of nitrobenzene, add dropwise 57.9 mmol of benzoyl chloride, at 12° C. and under nitrogen. Allow to react for 2 hours at 12° C. and pour the reaction mixture onto ice. Extract with dichloromethane, dry over magnesium sulfate, concentrate and then chromatograph the crude material on silica (eluent CH2Cl2 /CH3OH: 99/1).

Workup

  1. customat 12° C.
  2. customto react for 2 hours at 12° C.
  3. additionpour the reaction mixture onto ice
  4. extractionExtract with dichloromethane
  5. dry with materialdry over magnesium sulfate
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-98ff628678a445cab1d14cc6006afbcf
Source dataset
uspto-grants-1997_01
Patent number
US05591775

Reaction notes

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