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

HRID 29661

Reaction equation

HRID 29661 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-56588c6a396e49eca033e96f266f80bb
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Linked notes

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