4-Benzyl-9-methyl-7-(2-methyl-5-nitro-phenyl)-4,9-dihydro-3,4,9-triaza-cyclopenta[a]naphthalen-8-one → 7-(5-Amino-2-methyl-phenyl)-9-methyl-3,9-dihydro-3,4,9-triaza-cyclopenta[a]naphthalen-8-one

HRID 2261193Notes

Reaction equation

HRID 2261193 reaction equation
C([N:8]1[CH:17]=[C:16]2[C:11]([N:12]([CH3:29])[C:13](=[O:28])[C:14]([C:18]3[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:19]=3[CH3:27])=[CH:15]2)=[C:10]2[CH:30]=[CH:31][N:32]=[C:9]12)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:24][C:22]1[CH:21]=[CH:20][C:19]([CH3:27])=[C:18]([C:14]2[C:13](=[O:28])[N:12]([CH3:29])[C:11]3[C:16](=[CH:17][N:8]=[C:9]4[NH:32][CH:31]=[CH:30][C:10]4=3)[CH:15]=2)[CH:23]=1

Participants

4

Reactant 1

HCID 591985084-Benzyl-9-methyl-7-(2-methyl-5-nitro-phenyl)-4,9-dihydro-3,4,9-triaza-cyclopenta[a]naphthalen-8-one

Product 1

HCID 591985257-(5-Amino-2-methyl-phenyl)-9-methyl-3,9-dihydro-3,4,9-triaza-cyclopenta[a]naphthalen-8-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

4-Benzyl-9-methyl-7-(2-methyl-5-nitro-phenyl)-4,9-dihydro-3,4,9-triaza-cyclopenta[a]naphthalen-8-one (590 mg, 1.4 mmol) and 200 mg Pd(OH)2 in 20 ml ethanol is stirred under hydrogen atmosphere at room temperature for 12 hours. The reaction mixture is passed through a celite pad. The filtrate is concentrated and dried under vacuum to give the title compound as solid. MS m/z 305.2 (M+1).

Workup

  1. concentrationThe filtrate is concentrated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-a964c63483894adebaaeb2ea32eab291
Source dataset
uspto-grants-2010_12
Patent number
US07846923B2

Reaction notes

Loading…