Benzoyl chloride → 2-Chloro-5-benzoylaminopyridine

HRID 54662Notes

Reaction equation

HRID 54662 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](CN)=[CH:4][N:3]=1.C([N:12](CC)CC)C.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:12][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 70209275-(Aminomethyl)-2-chloropyridine

Product 1

HCID 97946482-Chloro-5-benzoylaminopyridineYield 105.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

14.25 g (0.1 mol) of 2-chloro-5-aminomethylpyridine and 11.1 g (0.11 mol) of triethylamine are dissolved in 150 ml of methylene chloride. 14.8 g (0.105 mol) of benzoyl chloride are then added dropwise at about 20° C. and the reaction mixture is subsequently stirred overnight at room temperature. It is washed three times with water and the organic phase is dried and concentrated. 24.6 g (99.8% of theory) of 2-chloro-5-benzoylaminopyridine are obtained as white crystals of melting point 118°-120° C.

Workup

  1. washIt is washed three times with water
  2. customthe organic phase is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f2161ce8085e4e71a9a2e8a6ca6c75aa
Source dataset
uspto-grants-1997_04
Patent number
US05623076

Reaction notes

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