Methyl 2-fluoro-3-nitrobenzoate → Methyl 3-amino-2-fluorobenzoate hydrochloride

HRID 534665Notes

Reaction equation

HRID 534665 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[F:13].[ClH:15].CO>[Pd].CO>[ClH:15].[NH2:10][C:6]1[C:5]([F:13])=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([O:2][CH3:1])=[O:14]

Participants

5

Reactant 2

HCID 13470961Methyl 2-fluoro-3-nitrobenzoateHCID 21893726Hydrochloride methanol

Product 1

HCID 67167731Methyl 3-amino-2-fluorobenzoate hydrochlorideYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Fluoro-3-nitrobenzoic acid methyl ester (9.10 g, 0.046 mol), 10% hydrochloric acid/methanol (25 ml), methanol (60 ml), and 5% palladium/carbon (50% wet product) (2.7 g) were introduced, and the reaction mixture was hydrogenated at room temperature. After completion of the reaction, the catalyst was filtered away, and the filtrate was concentrated under reduced pressure. The concentration residue was washed with diisopropyl ether, as a result of which 8.01 g (yield: 85%) of the indicated compound was obtained.

Workup

  1. customwas hydrogenated at room temperature
  2. customAfter completion of the reaction
  3. filtrationthe catalyst was filtered away
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washThe concentration residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-4ca83f54d0934a93b6ccb7a2892b52c0
Source dataset
uspto-grants-2014_10
Patent number
US08853440B2

Reaction notes

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