Benzyl 4-(aminocarbonyl)-3-(cyclohexylamino)benzoate → 4-(Aminocarbonyl)-3-(cyclohexylamino)benzoic acid

HRID 906148Notes

Reaction equation

HRID 906148 reaction equation
[NH2:1][C:2]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])=[CH:6][C:5]=1[NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:3].[H][H]>CO.[Pd]>[NH2:1][C:2]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:3]

Participants

5

Reactant 2

HCID 67403240Benzyl 4-(aminocarbonyl)-3-(cyclohexylamino)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 577481984-(Aminocarbonyl)-3-(cyclohexylamino)benzoic acidYield 74.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 4-(aminocarbonyl)-3-(cyclohexylamino)benzoate (45 mg, 0.128 mmol) in methanol (2 mL) was added palladium on carbon (10W %, Degussa type, 45 mg). The mixture was vigorously stirred under 1 atm of hydrogen for 50 minutes. The catalyst was removed by filtration through celite, and the filtrate was concentrated to provide 4-(aminocarbonyl)-3-(cyclohexylamino)benzoic acid (25 mg, 0.095 mmol, 74% yield) as a yellow powder. 1H NMR (400 MHz, CD3OD): 7.59 (d, 1H), 7.35 (s, 1H), 7.14 (dd, 1H), 3.47-3.39 (m, 1H), 2.05-1.98 (m, 2H), 1.81-1.73 (m, 2H), 1.68-1.60 (m, 1H), 1.52-1.41 (m, 2H), 1.38-1.25 (m, 3H).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1e086d0556bc4229aba7492d30d37609
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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