D-Psicose → Methyl 4-amino-2-fluoro-5-methoxybenzoate

HRID 1676529Notes

Reaction equation

HRID 1676529 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([N+:12]([O-])=O)=[CH:6][C:5]=1[F:15].OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([NH2:12])=[CH:6][C:5]=1[F:15]

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 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 702EthanolSolvent

Procedure

To a solution of 0.92 g (4.01 mmole) of 2-fluoro-5-methoxy-4-nitro-benzoic acid methyl ester and 30 mL of ethanol was added 0.10 g of 10% Pd/C. The mixture was hydrogenated in a Parr hydrogenator at 50 Psi for 1 day. The catalyst was removed by filtration and the solution was concentrated under reduced pressure to give 0.78 g of 4-amino-2-fluoro-5-methoxy-benzoic acid methyl ester.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b548311ba884407f87e0c592fc66bccd
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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