2-(4-Tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester → 4-Amino-2-(4-tert-butyl-benzoylamino)-benzoic acid methyl ester

HRID 1392260Notes

Reaction equation

HRID 1392260 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[NH:13][C:14](=[O:25])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[NH:13][C:14](=[O:25])[C:15]1[CH:16]=[CH:17][C:18]([C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 691945292-(4-Tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester

Product 1

HCID 691966714-Amino-2-(4-tert-butyl-benzoylamino)-benzoic acid methyl esterYield 76.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a Parr shaker bottle was added 10% Pd/C (0.346 g) then ethyl acetate (50 mL) followed by 2-(4-tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester (3.041 g, 8.53 mmol) as a solution in ethyl acetate (200 mL). The reaction was hydrogenated overnight, filtered through celite and silica washing with ethyl acetate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (20/80) to afford 4-amino-2-(4-tert-butyl-benzoylamino)-benzoic acid methyl ester (2.122 g, 76%) as a yellow solid.

Workup

  1. filtrationfiltered through celite and silica washing with ethyl acetate
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-db6a674a07a8411f85ab16bd819a538b
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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