4-Aminopyridine → Benzamide

HRID 1025911Notes

Reaction equation

HRID 1025911 reaction equation
[NH2:1]C1C=CN=CC=1.C(N(CC)CC)C.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[C:15]([NH2:1])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 2331BenzamideYield 122.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-aminopyridine (3.00 g, 31.9 mmol) in CH2Cl2 (50 mL) at 0° C. was added triethylamine (6.70 mL, 47.9 mmol) and benzoyl chloride (3.70 mL, 31.9 mmol). The ice bath was removed and the resulting mixture was allowed to warm tort over 1.5 h. The reaction was quenched with saturated aqueous NaHCO3, extracted with CH2Cl2, washed with brine, dried (MgSO4) and concentrated. The crude product was recrystallized from EtOAc/hexanes to give 4.73 g (75% yield) of pure benzamide.

Workup

  1. customThe ice bath was removed
  2. temperatureto warm tort over 1.5 h
  3. customThe reaction was quenched with saturated aqueous NaHCO3
  4. extractionextracted with CH2Cl2
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-fc133dd27c1c4b5abaa543296584e564
Source dataset
uspto-grants-2014_05
Patent number
US08729107B2

Reaction notes

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