Benzyl 4-azido-5-(benzyloxy)-2-((2-chlorophenyl)amino)-3-fluorobenzoate → 4-Amino-2-((2-chlorophenyl)amino)-3-fluoro-5-hydroxybenzoic acid

HRID 928969Notes

Reaction equation

HRID 928969 reaction equation
[N:1]([C:4]1[C:19]([O:20]CC2C=CC=CC=2)=[CH:18][C:7]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])=[C:6]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:5]=1[F:36])=[N+]=[N-].[H][H]>CO.[Pd]>[NH2:1][C:4]1[C:19]([OH:20])=[CH:18][C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:5]=1[F:36]

Participants

5

Reactant 2

HCID 89704804Benzyl 4-azido-5-(benzyloxy)-2-((2-chlorophenyl)amino)-3-fluorobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 897049294-Amino-2-((2-chlorophenyl)amino)-3-fluoro-5-hydroxybenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound benzyl 4-azido-5-(benzyloxy)-2-((2-chlorophenyl)amino)-3-fluorobenzoate (22.97 g, 45.67 mmol) in MeOH (500 mL) was added and 10% palladium on carbon (3.80 g) under nitrogen atmosphere. Then the nitrogen atmosphere was completely changed to hydrogen atmosphere. The mixture was stirred for 3 h at ambient temperature. After the insoluble matter was filtered off, the solvent was evaporated under reduced pressure to give the desired product, which was used directly in the next step without further purification.

Workup

  1. filtrationAfter the insoluble matter was filtered off
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-34d61e1047a5473283850ab251407c91
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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