Water → N-[2-(7-methoxy-1-naphthyl)ethyl]phthalimide

HRID 243631Notes

Reaction equation

HRID 243631 reaction equation
C1(S(O[CH2:11][CH2:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[CH:16]=[CH:15][CH:14]=2)(=O)=O)C=CC=CC=1.[C:25]1(=[O:35])[NH:29][C:28](=[O:30])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12.[K].O>CN(C)C=O>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17]([CH:16]=[CH:15][CH:14]=[C:13]2[CH2:12][CH2:11][N:29]2[C:28](=[O:30])[C:27]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]3[C:25]2=[O:35])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 135700677-Methoxy-1-naphthylethyl benzene sulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 44633448N-[2-(7-methoxy-1-naphthyl)ethyl]phthalimideYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound IV (14 g, 0.041 mol) produced as described above and potassium phthalimide (8.3 g, 0.045 mol) were added into a flask containing dimethylformamide (180 ml) as a solvent, heated and refluxed for 2 hours. After cooling the content to room temperature, 200 ml of water was added. The mixture was stirred and filtered. The filter cake formed was washed with water and dried, to produce 10.8 g of N-[2-(7-methoxy-1-naphthyl)ethyl]phthalimide (II). The yield was 80%. The melting point was 159-160° C.

Workup

  1. additionwere added into a flask
  2. temperatureheated
  3. temperaturerefluxed for 2 hours
  4. filtrationfiltered
  5. customThe filter cake formed
  6. washwas washed with water
  7. customdried

Sources & evidence

ORD record
ord-e60ec5d901e54a1b8e1a3dc01b401fa6
Source dataset
uspto-grants-2014_02
Patent number
US08653281B2

Reaction notes

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