Hydrazine → 2-Amino-4-bromobenzoic acid

HRID 1592941Notes

Reaction equation

HRID 1592941 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-])=O)[CH:3]=1.[OH-].[Na+].NN>[Fe](Cl)(Cl)Cl.C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 14798Sodium HydroxideHCID 37744674-Bromo-2-nitrobenzoic acid

Product 1

HCID 886912-Amino-4-bromobenzoic acidYield 102.3%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

To 4-bromo-2-nitrobenzoic acid (1.80 g, 7.83 mmol) were added 0.88N aqueous sodium hydroxide solution (10 mL), iron(III) chloride (133 mg) and isopropyl alcohol (0.7 mL) and the mixture heated to 75° C. While stirring the mixture, hydrazine (1.1 mL) was slowly added, and the mixture was reacted at 75° C. for 2 hrs. The reaction mixture was filtered and the filtrate was concentrated. The precipitated solid was washed with water to give 4-bromoanthranilic acid (1.73 g, 96%).

Workup

  1. additionwas slowly added
  2. customthe mixture was reacted at 75° C. for 2 hrs
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. washThe precipitated solid was washed with water

Sources & evidence

ORD record
ord-b8303bf7a8fa426b9e6644d1468bf63c
Source dataset
uspto-grants-2007_11
Patent number
US07294629B2

Reaction notes

Loading…