Acetyl chloride → 2-Acetamido-5-nitropyridine

HRID 257429

Reaction equation

HRID 257429 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(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:18]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 778882-Amino-5-nitropyridine

Product 1

HCID 3451252-Acetamido-5-nitropyridineYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-5-nitropyridine (4.0 g, 28.8 mmol) in dichloromethane (15 ml) were added 176 mg (31.6 mmol) of 4-N,N'-dimethylaminopyridine (DMAP), 4.41 ml of triethylamine (31.6 mmol) and 2.16 ml (31.6 mmol) of acetyl chloride in turn, and the mixture was stirred at room temperature for 1 hour. A 1 M aqueous solution of potassium carbonate was added to the mixed suspension to neutralize it. Extraction with chloroform was repeated three times, and the extract was dried over magnesium sulfate. The solvent was removed, and the residue was subjected to silica gel column chromatography (eluent: chloroform). Recrystallization from chloroform-hexane gave 2.14 g of the intended product as a flesh-colored powder (yield: 49%).

Workup

  1. extractionExtraction with chloroform
  2. dry with materialthe extract was dried over magnesium sulfate
  3. customThe solvent was removed
  4. customRecrystallization from chloroform-hexane

Sources & evidence

ORD record
ord-73c9e560c9684380bd116308f47e6239
Source dataset
uspto-grants-1993_11
Patent number
US05262415

Linked notes

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