Benzoic acid, 2-amino-5-fluoro-3-nitro- (9CI) → 2,3-Diamino-5-fluoro-benzoic acid

HRID 85181Notes

Reaction equation

HRID 85181 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][C:8]([F:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H][H]>[Pd].CO>[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][C:8]([F:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 18548624Benzoic acid, 2-amino-5-fluoro-3-nitro- (9CI)HCID 178418361HCID 178418361, compound

Product 1

HCID 224111292,3-Diamino-5-fluoro-benzoic acidYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Amino-5-fluoro-3-nitrobenzoic acid (142; 0.73 g) was dissolved into methanol (10 mL). To this solution was added 5% Pd/C (0.1 g). The resulting reaction mixture was stirred at room temperature under 1 atm of hydrogen for 18 h and then filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to afford 2,3-diamino-5-fluorobenzoic acid 143 as a brown solid (0.59 g, 95%).

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c268dffc07e847ed9ffea93fc1477c06
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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