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

HRID 243634Notes

Reaction equation

HRID 243634 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].CN(C)C=O>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 6228DimethylformamideHCID 135700677-Methoxy-1-naphthylethyl benzene sulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 44633448N-[2-(7-methoxy-1-naphthyl)ethyl]phthalimideYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound IV (14 g, 0.041 mol) produced as described above and potassium phthalimide (12.3 g, 0.0656 mol) were added into a reaction vessel, and dimethylformamide (200 ml) was added. The mixture was heated and refluxed for 2 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 12.3 g of N-[2-(7-methoxy-1-naphthyl)ethyl]phthalimide (II). The yield was 92.3%. The melting point was 160-161° C.

Workup

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

Sources & evidence

ORD record
ord-bd516e09ae6c4b62b1cd0dc0f817b780
Source dataset
uspto-grants-2014_02
Patent number
US08653281B2

Reaction notes

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