Isonicotinic Acid → N-(2-Aminophenyl)pyridine-4-carboxamide

HRID 568402Notes

Reaction equation

HRID 568402 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:22]1([NH2:29])[C:23]([NH2:28])=[CH:24][CH:25]=[CH:26][CH:27]=1>ClCCl>[NH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:29][C:7]([C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)=[O:9]

Participants

5

Reactant 3

HCID 5922Isonicotinic AcidHCID 7243O-PhenylenediamineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 1133081N-(2-Aminophenyl)pyridine-4-carboxamideYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred suspension of 4-pyridinecarboxylic acid (2.15 g, 17.5 mmol) in dichloromethane (40 ml) was treated with 1,1'-carbonyldiimidazole (3.115 g, 19.2 mmol) and the resulting solution was stirred for 85 minutes and added to 1,2-benzenediamine (3.777 g, 34.9 mmol) in dichloromethane (125 ml). After 3 hours, the precipitate formed was filtered and purified by chromatography (SiO2 ; ethyl acetate) to give the title compound as pale yellow crystals (1.267 g), m.p. 225°-235°.

Workup

  1. waitAfter 3 hours
  2. customthe precipitate formed
  3. filtrationwas filtered
  4. custompurified by chromatography (SiO2 ; ethyl acetate)

Sources & evidence

ORD record
ord-aa167ff460c14a9a961b59e1a391c0e4
Source dataset
uspto-grants-1988_03
Patent number
US04728658

Reaction notes

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