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

HRID 522914Notes

Reaction equation

HRID 522914 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]>CO.[Pd]>[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 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-fluoro-N-methyl-5-nitrobenzamide (500 mg, 2.52 mmoL) in methanol (7.5 mL) was added Pd/C (30%) and the mixture was stirred at RT for 1 h. The reaction mixture was filtered through Celite® (diatomaceous earth), washed with methanol and concentrated under reduced. Purification by silica gel column chromatography provided 3-amino-5-fluoro-N-methylbenzamide (0.300 g, 75%) as a solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite® (diatomaceous earth)
  2. washwashed with methanol
  3. concentrationconcentrated under reduced
  4. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-932148e60f4240bfa7abda7a048f692e
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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