Acetic Anhydride → 2-Acetamido-5-nitropyridine

HRID 276846

Reaction equation

HRID 276846 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:11]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 778882-Amino-5-nitropyridine

Product 1

HCID 3451252-Acetamido-5-nitropyridine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

2-Amino-5-nitropyridine was treated with acetic anhydride in dry pyridine in the presence of 4-dimethylaminopyridine at room temperature for 24 hrs under argon. The solvent was removed by rotary evaporation. The residue was dissolved in CH2Cl2, and ether was added to form a solid. The white solid was collected and dried giving 2-acetamido-5-nitropyridine. Hydrogenation of this material using 10%Pd on C in MeOH at room temperature under atmospheric pressure gave 2-acetamido-5-aminopyridine.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. additionether was added
  4. customto form a solid
  5. customThe white solid was collected
  6. customdried

Sources & evidence

ORD record
ord-0dc588cad01a499ab6e8b0dc91da72e7
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Linked notes

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