Benzoic acid, 4-amino-2,3-difluoro-5-nitro-, methyl ester → Methyl 4,5-diamino-2,3-difluorobenzoate

HRID 1514907Notes

Reaction equation

HRID 1514907 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH2:13])=[C:6]([F:14])[C:5]=1[F:15]>CCO.O=[Pt]=O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:13])=[C:6]([F:14])[C:5]=1[F:15]

Participants

4

Reactant 1

HCID 2759749Benzoic acid, 4-amino-2,3-difluoro-5-nitro-, methyl ester

Product 1

HCID 86651263Methyl 4,5-diamino-2,3-difluorobenzoate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-amino-2,3-difluoro-5-nitrobenzoic acid methyl ester (500 mg, 2.2 mmol) in EtOH (20 ml) was added PtO2 (50 mg, 10% w). The suspension was hydrogenated with a H2 balloon overnight. The catalyst was filtered through Celite and washed with EtOH The solvent was removed under reduced pressure to give 4,5-diamino-2,3-difluorobenzoic acid methyl ester as a light yellow solid.

Workup

  1. customwas hydrogenated with a H2 balloon overnight
  2. filtrationThe catalyst was filtered through Celite
  3. washwashed with EtOH The solvent
  4. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-36d49e8dd07644c893acb3820074e294
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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