2-(1-Methylethoxy)-5-nitrobenzoic acid → 5-Amino-2-[(propan-2-yl)oxy]benzoic acid

HRID 2098399Notes

Reaction equation

HRID 2098399 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])([CH3:3])[CH3:2]>CCO.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 44473202-(1-Methylethoxy)-5-nitrobenzoic acid

Product 1

HCID 160422975-Amino-2-[(propan-2-yl)oxy]benzoic acidYield 79.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Isopropoxy-5-nitrobenzoic acid (6.02 g, 26.75 mmol) was suspended in EtOH (100 ml) and 10% Pd on C (wet basis) (600 mg) was added. The mixture was hydrogenated at 50 psi for 2 hrs. The mixture was filtered through celite and the volatiles were removed in vacuo. The residue was triturated with IPA, and the resulting solid filtered off, washed with MTBE and dried in vacuo to give 4.15 g of 5-amino-2-isopropoxybenzoic acid (79.5%) as a pale yellow solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe volatiles were removed in vacuo
  3. customThe residue was triturated with IPA
  4. filtrationthe resulting solid filtered off
  5. washwashed with MTBE
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8226a06bf1a54932ac3e629aad9e3ab9
Source dataset
uspto-grants-2013_05
Patent number
US08450506B2

Reaction notes

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