4-Nitrobenzoyl-1,3-dihydroimidazol-2-one → 4-Aminobenzoyl-1,3-dihydroimidazol-2-one

HRID 1348952Notes

Reaction equation

HRID 1348952 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([C:8]([N:10]2[CH:14]=[CH:13][NH:12][C:11]2=[O:15])=[O:9])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:17]=[CH:16][C:7]([C:8]([N:10]2[CH:14]=[CH:13][NH:12][C:11]2=[O:15])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 210928284-Nitrobenzoyl-1,3-dihydroimidazol-2-one

Product 1

HCID 210928274-Aminobenzoyl-1,3-dihydroimidazol-2-oneYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1b (200 mg, 0.86 mmol) in 20 mL MeOH was hydrogenated over 10% Pd/C (40 mg) at 50 psi H2. The reaction mixture was filtered through a plug of Celite®, washed with MeOH and concentrated on a rotary evaporator to give 168 mg (98% yield) of 4-aminobenzoyl-1,3-dihydroimidazol-2-one 1c. MS found: (M+H)+=204.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite®
  2. washwashed with MeOH
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-1ac651baa03c4e54aa987366e32b7de2
Source dataset
uspto-grants-2007_05
Patent number
US07211671B2

Reaction notes

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