Phthalic Anhydride → 2-(2-Chloropyridin-3-yl)-1H-isoindole-1,3(2H)-dione

HRID 615947Notes

Reaction equation

HRID 615947 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[C:14]([Cl:19])=[N:15][CH:16]=[CH:17][CH:18]=1.C1(C)C(S(O)(=O)=O)=CC=CC=1>ClC1C=CC=CC=1Cl>[Cl:19][C:14]1[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])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 69252-Methylbenzenesulfonic acidHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 545217332-(2-Chloropyridin-3-yl)-1H-isoindole-1,3(2H)-dioneYield 99%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
30 °C

Procedure

A stirred slurry containing 15 grams of phthalic anhydride, 13 grams of 3-amino-2-chloropyridine, one gram of toluenesulfonic acid and 200 ml. of o-dichlorobenzene was heated at reflux for 6 hours. During this heating period 100 ml. of solvent and 1.8 ml. of water were removed. After cooling to 30° C., 50 ml. of heptane and 10 ml. of water were added and stirring was continued. The solid was collected by filtration and air dried. A 99 percent yield of N-(2-chloro-3-pyridyl) phthalimide, m.p. 156°-7° C., was obtained.

Workup

  1. temperatureat reflux for 6 hours
  2. waitDuring this heating period 100 ml
  3. customof water were removed
  4. additionof water were added
  5. filtrationThe solid was collected by filtration and air
  6. customdried

Sources & evidence

ORD record
ord-12c0904d149d451db2bbed467ef416e9
Source dataset
uspto-grants-1978_02
Patent number
US04072499

Reaction notes

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