3-Iodo-p-toluidine → 2-Chloro-N-(3-iodo-4-methylphenyl)pyridine-4-carboxamide

HRID 1988875Notes

Reaction equation

HRID 1988875 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.[I:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[CH3:19])[NH2:15]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([NH:15][C:14]1[CH:16]=[CH:17][C:18]([CH3:19])=[C:12]([I:11])[CH:13]=1)=[O:7]

Participants

4

Reactant 2

HCID 1188893-Iodo-p-toluidineHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 219145572-Chloro-N-(3-iodo-4-methylphenyl)pyridine-4-carboxamideYield 89.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloroisonicotinic acid (3.3 g) HATU (8.75 g) DIPEA (10.9 ml) and 3-iodo-4-methylaniline (5.00 g) in DMF (50 ml) were heated under nitrogen for 16 h. The reaction was cooled, the solvent was removed under vacuum and the residue was dissolved in dichloromethane (150 ml). The solution was washed with water (3×100 ml) and brine (100 ml) dried (magnesium sulphate) and the solvent was removed under vacuum. The residue was purified by column chromatography on silica eluting with ethyl acetate/cyclohexane (40:60) to give the title compound as a white solid (7.00 g).

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent was removed under vacuum
  3. dissolutionthe residue was dissolved in dichloromethane (150 ml)
  4. washThe solution was washed with water (3×100 ml) and brine (100 ml)
  5. dry with materialdried (magnesium sulphate)
  6. customthe solvent was removed under vacuum
  7. customThe residue was purified by column chromatography on silica eluting with ethyl acetate/cyclohexane (40:60)

Sources & evidence

ORD record
ord-8d8c0277e1f44a97a1507487e1a07a55
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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