HCID 22987966, compound → HCID 11074797, compound

HRID 429192Notes

Reaction equation

HRID 429192 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[NH:14]C(=O)C(C)(C)C)=[O:7])=[CH:4][CH:3]=1>Cl>[NH2:14][C:13]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[C:6](=[O:7])[C:5]1[CH:21]=[CH:22][C:2]([F:1])=[CH:3][CH:4]=1

Participants

3

Reactant 1

HCID 22987966HCID 22987966, compound

Product 1

HCID 11074797HCID 11074797, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-[3-(4-fluorobenzoyl)pyridin-4-yl]-2,2-dimethylpropanamide (2.85 g, 9.5 mmol) in 3 N aqueous HCl (15 ml) was warmed at reflux overnight. After cooling to room temperature, the reaction mixture was washed with ether, the aqueous layer was separated and neutralized with potassium carbonate. The product was extracted into ethyl acetate, dried over potassium carbonate/sodium carbonate and concentrated. The residue was purified by flash chromatography (5% methanol/methylene chloride gradient) to afford 4-amino-3-(4-fluorobenzoyl)pyridine (1.58 g).

Workup

  1. temperatureat reflux overnight
  2. washthe reaction mixture was washed with ether
  3. customthe aqueous layer was separated
  4. extractionThe product was extracted into ethyl acetate
  5. dry with materialdried over potassium carbonate/sodium carbonate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (5% methanol/methylene chloride gradient)

Sources & evidence

ORD record
ord-18d0c09bcb694513bb77de4cc3891b81
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Reaction notes

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