Ammonium Hydroxide → 4-Chloropyridine-2-carboxamide

HRID 491675Notes

Reaction equation

HRID 491675 reaction equation
[NH4+:1].[OH-].[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10](Cl)=[O:11])[CH:5]=1.CC(OC)(C)C>CCOC(C)=O>[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([NH2:1])=[O:11])[CH:5]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 15413tert-Butyl methyl etherHCID 110951464-chloropyridine-2-carbonyl Chloride

Product 1

HCID 3035434-Chloropyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Aqueous NH4OH (40%, 250 mL) was added dropwise at 0° C. to a suspension of 4-chloro-pyridine-2-carbonyl chloride (75 g, 533 mmol) in EtOAc. Upon addition, the temperature rose to 30° C. The mixture was stirred for 2 h at RT then kept at RT for 12 h without stirring. MTBE (250 mL) was added to the mixture and the resulting emulsion was filtered. The solid was washed with EtOAc. The MTBE/EtOAc layer was washed twice with water and once with 5% Na2CO3, then dried over MgSO4 and concentrated under vacuum. The resulting solid was suspended in EtOAc several times and filtered out to give the desired compound.

Workup

  1. additionUpon addition
  2. customrose to 30° C
  3. waitthen kept at RT for 12 h
  4. stirringwithout stirring
  5. filtrationthe resulting emulsion was filtered
  6. washThe solid was washed with EtOAc
  7. washThe MTBE/EtOAc layer was washed twice with water and once with 5% Na2CO3
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under vacuum
  10. filtrationfiltered out

Sources & evidence

ORD record
ord-f7398dab32414e60812d91361729e218
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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