3-fluoro-N-methyl-5-nitrobenzamide → 3-amino-5-fluoro-N-methylbenzamide

HRID 522846Notes

Reaction equation

HRID 522846 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)[C:5]([NH:7][CH3:8])=[O:6]>[Pd].CCO>[NH2:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([F:1])[CH:11]=1)[C:5]([NH:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 594427293-fluoro-N-methyl-5-nitrobenzamide

Product 1

HCID 673547273-amino-5-fluoro-N-methylbenzamideYield 101.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a roundbottom flask charged with 3-fluoro-N-methyl-5-nitrobenzamide (961 mg, 4.85 mmol) was added EtOH (16 mL). The resulting suspension was thoroughly purged with nitrogen prior to the addition of 10% Pd/C (43 mg, 0.485 mmol). The reaction mixture was purged with H2 (g), then stirred under 1 atm. H2 balloon at RT. After 2 d, the reaction mixture was filtered through Celite® (diatomaceous earth) with the aid of EtOH and the filtrate was dried under reduced pressure to afford 3-amino-5-fluoro-N-methylbenzamide (825 mg, 4.91 mmol, 100%).

Workup

  1. customThe resulting suspension was thoroughly purged with nitrogen
  2. customThe reaction mixture was purged with H2 (g)
  3. customat RT
  4. filtrationthe reaction mixture was filtered through Celite® (diatomaceous earth) with the aid of EtOH
  5. customthe filtrate was dried under reduced pressure

Sources & evidence

ORD record
ord-65056796dbff4bf9892b7f4dde29c0b8
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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