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

HRID 243633Notes

Reaction equation

HRID 243633 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].C(#N)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 6342AcetonitrileHCID 135700677-Methoxy-1-naphthylethyl benzene sulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 44633448N-[2-(7-methoxy-1-naphthyl)ethyl]phthalimideYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound IV (14 g, 0.041 mol) produced as described above and potassium phthalimide (10.8 g, 0.0574 mol) were added into a reaction vessel, and acetonitrile (150 ml) was added. The mixture was heated and refluxed for 4 hours. After cooling it to room temperature, 200 ml of water was added, and the mixture was stirred and filtered. The filter cake formed was washed with water and dried, to produce 12 g of N-[2-(7-methoxy-1-naphthyl)ethyl]phthalimide (II). The yield was 90%. The melting point was 160-160.9° C.

Workup

  1. additionwere added into a reaction vessel
  2. temperatureThe mixture was heated
  3. temperaturerefluxed for 4 hours
  4. filtrationfiltered
  5. customThe filter cake formed
  6. washwas washed with water
  7. customdried

Sources & evidence

ORD record
ord-d653e165224d42edb2bb4e9ef7e3991e
Source dataset
uspto-grants-2014_02
Patent number
US08653281B2

Reaction notes

Loading…