Methyl 2-fluoro-4-(4-methoxybenzylamino)-5-nitrobenzoate → Methyl 5-amino-2-fluoro-4-(4-methoxybenzylamino)benzoate

HRID 1403601Notes

Reaction equation

HRID 1403601 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:9]([N+:22]([O-])=O)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[Pd]>[NH2:22][C:9]1[C:10]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:11][C:2]([F:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 70664665Methyl 2-fluoro-4-(4-methoxybenzylamino)-5-nitrobenzoate

Product 1

HCID 70665225Methyl 5-amino-2-fluoro-4-(4-methoxybenzylamino)benzoateYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-fluoro-4-(4-methoxybenzylamino)-5-nitrobenzoate (50.0 g, 149.57 mmol) in methanol (1500 ml) was added palladium on carbon (15 g). The mixture was allowed to react for 2 hours at room temperature under an atmosphere of H2 (g). The solids were filtered out and the filtrate was concentrated in vacuo to afford methyl 5-amino-2-fluoro-4-(4-methoxybenzylamino)benzoate as a gray solid (30.0 g, 66%).

Workup

  1. customto react for 2 hours at room temperature under an atmosphere of H2 (g)
  2. filtrationThe solids were filtered out
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5ee76ecd98864c55a92161397f939464
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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