2-Aminopyridine → N-(2-pyridyl)-4-chlorophthalimide

HRID 1816021Notes

Reaction equation

HRID 1816021 reaction equation
[Cl:1][CH:2]1[CH:12]=[CH:11][CH:5]2[C:6]([O:8][C:9](=[O:10])[CH:4]2[CH2:3]1)=O.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>ClC1C(Cl)=C(Cl)C=CC=1>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:13]1[C:9](=[O:10])[C:4]2=[CH:3][C:2]([Cl:1])=[CH:12][CH:11]=[C:5]2[C:6]1=[O:8]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 54187688HCID 54187688, compound

Product 1

HCID 4329505N-(2-pyridyl)-4-chlorophthalimideYield 84%

Reagents, catalysts & solvents 1

HCID 68951,2,3-TrichlorobenzeneSolvent

Procedure

5.2 grams of 4-chlorotetrahydrophthalic anhydride, 2.6 grams of 2-aminopyridine, 50 milliliters of trichlorobenzene and 6.0 grams of Calgon Carbon S-Sorb was combined in a 3 neck flask. The flask was fitted with a reflux condenser and an inlet tube adjusted to deliver air as bubbles below the surface. The third neck was fitted with a drying tube to remove water. After about 9 hours, N-(2-pyridyl)-4-chlorophthalimide was formed in about 84% yield as determined by GC-MS.

Workup

  1. customThe flask was fitted with a reflux condenser and an inlet tube
  2. customThe third neck was fitted with a drying tube
  3. customto remove water

Sources & evidence

ORD record
ord-94035aa56f0d423395ae981a716e2d53
Source dataset
uspto-grants-2005_04
Patent number
US06881815B2

Reaction notes

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