2-Nitro-5-(propan-2-yloxy)benzoic acid → 2-Amino-5-(propan-2-yloxy)benzoic acid

HRID 1070400Notes

Reaction equation

HRID 1070400 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-])=O)=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([NH2:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 127191792-Nitro-5-(propan-2-yloxy)benzoic acid

Product 1

HCID 127191892-Amino-5-(propan-2-yloxy)benzoic acidYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-isopropoxy-2-nitro-benzoic acid (946 mg, 4.2 mmol) in THF (15 mL) was added 5% Pd/C (95 mg) under a nitrogen atmosphere. A balloon filled with H2 was set up. The mixture was stirred for 3.5 h and filtered. The filtrate was dried to yield 816 mg of 5-isopropoxy-2-amino-benzoic acid.

Workup

  1. additionA balloon filled with H2
  2. filtrationfiltered
  3. customThe filtrate was dried

Sources & evidence

ORD record
ord-4a316e0375d44092a577e0de114a7457
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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