5-Fluoro-N-methyl-2-nitrobenzamide → 2-Amino-5-fluoro-N-methylbenzamide

HRID 1947850Notes

Reaction equation

HRID 1947850 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-])=O)=[C:6]([CH:11]=1)[C:7]([NH:9][CH3:10])=[O:8]>CCO.[Pd]>[NH2:12][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:11][C:6]=1[C:7]([NH:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 442030775-Fluoro-N-methyl-2-nitrobenzamide2×

Product 1

HCID 431325582-Amino-5-fluoro-N-methylbenzamideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-fluoro-N-methyl-2-nitrobenzamide (Compound 102B) in EtOH (10.0 mL) was charged with Palladium 10% wt on activated carbon (0.316 g, 0.297 mmol). The reaction mixture was evacuated and purged with hydrogen gas (3 times). The reaction mixture was allowed to stir under hydrogen at rt for 16 h. The reaction mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure to yield a light yellow semi-solid. The material was purified by silica gel chromatography using DCM/MeOH (100:0→95:5) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield a white solid, 0.500 g (100% yield). 1H NMR (CDCl3, 400 MHz): δ=2.98 (d, J=4.80 Hz, 3H), 5.30 (d, J=5.31 Hz, 1H), 6.64 (dd, J=8.84, 4.80 Hz, 1H), 6.96 (ddd, J=8.91, 7.89, 2.91 Hz, 1H), 7.02 (dd, J=9.22, 2.91 Hz, 1H). MS (ES+): m/z 169.08 [MH+] (TOF, polar).

Workup

  1. customThe reaction mixture was evacuated
  2. custompurged with hydrogen gas (3 times)
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto yield a light yellow semi-solid
  6. customThe material was purified by silica gel chromatography
  7. additionThe fractions containing product
  8. concentrationconcentrated under reduced pressure
  9. customto yield a white solid, 0.500 g (100% yield)

Sources & evidence

ORD record
ord-2551509369d84dd0bdae3c365b124c90
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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