Ammonia → 3,5-Dichloroisonicotinamide

HRID 23889Notes

Reaction equation

HRID 23889 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:11])[C:7]=1[C:8](Cl)=[O:9].C(Cl)Cl.[NH3:15]>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:11])[C:7]=1[C:8]([NH2:15])=[O:9]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6344DichloromethaneHCID 115720223,5-Dichloropyridine-4-carbon chloride

Product 1

HCID 28029113,5-Dichloroisonicotinamide

Conditions

Temperature
0 °C

Procedure

3,5-Dichloropyridine-4-carboxylic acid chloride (0.54 g, 2.6 mmol) was dissolved in CH2Cl2 (2.6 mL, 2.6 mmol) and NH3 (2.0 M in dioxane) (6.5 mL) was added. The reaction mixture was cooled to 0° C. for 30 min. The residue was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by preparative HPLC on silica gel to yield 3,5-dichloropyridine-4-carboxamide (0.135 g).

Workup

  1. customThe residue was quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by preparative HPLC on silica gel

Sources & evidence

ORD record
ord-4d47e79f6a5c4923bcb9e58c1c40a735
Source dataset
uspto-grants-2005_02
Patent number
US06855708B2

Reaction notes

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