Methyl 2,6-Difluoro-3-nitrobenzoate → Methyl 3-amino-2,6-difluorobenzoate

HRID 239451Notes

Reaction equation

HRID 239451 reaction equation
[F:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[C:8]([F:15])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[Pd]>[NH2:12][C:11]1[C:2]([F:1])=[C:3]([C:8]([F:15])=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 43449035Methyl 2,6-Difluoro-3-nitrobenzoate

Product 1

HCID 45480188Methyl 3-amino-2,6-difluorobenzoateYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 2,6-difluoro-3-nitrobenzoate (25 g, 115 mmol) in MeOH (150 mL) was added 5% palladium on carbon (2.5 g). The mixture was stirred under H2 atmosphere (50 psi/25° C.) for 12 h. The catalyst was filtered, and the filtrate was concentrated under the reduced pressure to dryness to give the product of Step C (20 g, 93.0%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.95-7.10 (m, 2H), 3.86 (s, 3H)

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated under the reduced pressure to dryness

Sources & evidence

ORD record
ord-ef4fb7404a214b998057ef5e7c7619fa
Source dataset
uspto-grants-2014_02
Patent number
US08642759B2

Reaction notes

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