Phthalic Anhydride → N-(5-Chloro-2-pyridyl)phthalimide

HRID 615946Notes

Reaction equation

HRID 615946 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][N:14]=1>C1(C)C(C)=CC=CC=1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([N:12]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 661742-Amino-5-chloropyridine

Product 1

HCID 554989N-(5-Chloro-2-pyridyl)phthalimideYield 89%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred solution at 120° C. containing 30 grams of phthalic anhydride in 500 ml. of xylene, 26 grams of 2-amino-5-chloropyridine was added in one portion. The stirred solution was heated at reflux for 4 to 5 hours during which time 3.6 ml. of water was removed. After stirring at 25°-30° C. for 18 hours, the slurry was cooled to 5° C., the solids collected by filtration and air dried at 25°-30° C. An 89 percent yield of N-(5-chloro-2-pyridyl)phthalimide, m.p. 153°-5° C., was obtained.

Workup

  1. temperatureThe stirred solution was heated
  2. temperatureat reflux for 4 to 5 hours during which time 3.6 ml
  3. customof water was removed
  4. filtrationthe solids collected by filtration and air
  5. customdried at 25°-30° C

Sources & evidence

ORD record
ord-c4368b19af9d454382b959faedc0c661
Source dataset
uspto-grants-1978_02
Patent number
US04072499

Reaction notes

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