2-(4-Fluoro-5-nitrobenzoyl)-3-methylpyridine → 3-Amino-4-fluorophenyl 3-methyl-2-pyridyl ketone

HRID 48974Notes

Reaction equation

HRID 48974 reaction equation
[F:1][C:2]1[C:16]([N+:17]([O-])=O)=[CH:15][C:5]([C:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1>[Fe].C(O)(=O)C>[CH3:14][C:13]1[C:8]([C:6]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[C:16]([NH2:17])[CH:15]=2)=[O:7])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 206342552-(4-Fluoro-5-nitrobenzoyl)-3-methylpyridine

Product 1

HCID 120568333-Amino-4-fluorophenyl 3-methyl-2-pyridyl ketoneYield 73.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a mixture of 2-(4-fluoro-5-nitrobenzoyl)-3-methylpyridine (7.13 g, 0.0258 mol) and glacial acetic acid at 70-80° C. is added iron powder (7.76 g, 0.130 mol) in three portions. The resultant mixture is stirred overnight at 70-80° C., cooled to room temperature and extracted three times with ethyl acetate. The combined organic layers are filtered through Celite, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford the title compound as a tan solid (4.36 g, 69.8%) which is identified by NMR spectral analysis.

Workup

  1. extractionextracted three times with ethyl acetate
  2. filtrationThe combined organic layers are filtered through Celite
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a960065e0924f689f305d413ebcea84
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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