Methyl 2-fluoro-5-methoxy-4-nitrobenzoate → Methyl 4-amino-2-fluoro-5-methoxybenzoate

HRID 219866Notes

Reaction equation

HRID 219866 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-])=O)[C:9]([O:15][CH3:16])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[Pd]>[NH2:12][C:10]1[C:9]([O:15][CH3:16])=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1

Participants

4

Reactant 1

HCID 67076410Methyl 2-fluoro-5-methoxy-4-nitrobenzoate

Product 1

HCID 57955533Methyl 4-amino-2-fluoro-5-methoxybenzoateYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-fluoro-5-methoxy-4-nitrobenzoate (549 mg; 1.13 mmol; 1 eq.) was dissolved in MeOH (50 mL). The resulting solution was injected on a flow hydrogenation reactor (H-Cube), adapted with Pd/C cartridge (44 mm), a flow of 1 mL/min, a temperature of 60° C. and the full H2 option enabled. Solvents were evaporated, affording the title product as an off-white solid (220 mg; 97%). LC/MS (Method B): 200.0 (M+H)+. HPLC (Method A) Rt 3 min (Purity: 91.9%).

Workup

  1. customThe resulting solution was injected on a flow hydrogenation reactor
  2. customa temperature of 60° C.
  3. customSolvents were evaporated

Sources & evidence

ORD record
ord-dc4443a2126b496988c907898b32512d
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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