Methanol → Methyl 4-amino-3-fluorobenzoate

HRID 1748156Notes

Reaction equation

HRID 1748156 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)[C:5]([O:7][CH3:8])=[O:6].CO.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 887MethanolHCID 592761Methyl 3-fluoro-4-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 11182865Methyl 4-amino-3-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Into a 2000-mL round-bottom flask maintained with a nitrogen atmosphere, was placed a solution of methyl 3-fluoro-4-nitrobenzoate (98 g, 492.46 mmol, 1.00 equiv) in ethyl acetate:methanol=1:1 (1000 mL). Then Pd/C (10 g, 10 wt %, Degussa type) was added. The flask was fitted with a balloon of hydrogen, and the heterogeneous reaction mixture was stirred fo(16 h under a hydrogen atmosphere at 30°C. The catalyst solids were filtered off and the filtrate was concentrated under vacuum to give the deisred product methyl 4-amino-3-fluorobenzoate.

Workup

  1. temperatureInto a 2000-mL round-bottom flask maintained with a nitrogen atmosphere
  2. custom16 h
  3. customat 30°C
  4. filtrationThe catalyst solids were filtered off
  5. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-7e692409a4ca43359ef90b46cb3a1a7b
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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