Water → N-[4-chloro-2-(2-naphthoylamino)phenyl]phthalimide

HRID 277433Notes

Reaction equation

HRID 277433 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].C(N(CC)CC)C.[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[C:37](Cl)=[O:38].O>O1CCCC1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])=[C:2]([NH:1][C:37]([C:28]2[CH:29]=[CH:30][C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:27]=2)=[O:38])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 12650879N-(2-amino-4-chlorophenyl)phthalimide

Product 1

HCID 18615638N-[4-chloro-2-(2-naphthoylamino)phenyl]phthalimideYield 44.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A reaction solution of N-(2-amino-4-chlorophenyl)phthalimide (0.5 g), triethylamine (0.28 g) and 2-naphthoyl chloride (0.35 g) in anhydrous tetrahydrofuran (50 ml) was heated at reflux temperature for 6 hr under nitrogen atmosphere. The resulting mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine (×2) and dried over anhydrous sodium sulfate. The solvent was removed and the residue was purified by column chromatography on silica gel using ethyl acetate-hexane (1:5) to give the title compound (0.35 g) as a yellow solid.

Workup

  1. temperatureat reflux temperature for 6 hr under nitrogen atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine (×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bfa5a822283b4a3390a8762b53b8d166
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

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