(+/-)-5'-Amino-6'-nitro-3-methyl-spiro[imidazolidine-4,2'-indane]-2,5-dione → 5',6'-Diamino-3-methyl-spiro[imidazolidine-4,2'-indane]2,5-dione

HRID 656402Notes

Reaction equation

HRID 656402 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[CH2:7][C:6]1([C:17](=[O:18])[NH:16][C:15](=[O:19])[N:14]1[CH3:20])[CH2:5]2>CO.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[CH2:7][C:6]1([C:17](=[O:18])[NH:16][C:15](=[O:19])[N:14]1[CH3:20])[CH2:5]2

Participants

4

Reactant 1

HCID 67251733(+/-)-5'-Amino-6'-nitro-3-methyl-spiro[imidazolidine-4,2'-indane]-2,5-dione

Product 1

HCID 577741935',6'-Diamino-3-methyl-spiro[imidazolidine-4,2'-indane]2,5-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (±)-5′-amino-6′-nitro-spiro[imidazolidine-4,2′-indane]-2,5-dione from Step A (15 mg, 0.054 mmol) in MeOH (5 mL) was added 10% Pd/C (5 mg) and the reaction mixture was stirred vigorously under hydrogen (ca. 1 atm). After 2 h, the catalyst was filtered off and the filtrate was concentrated in vacuo to yield the title compound. MS: m/z=247 (M+1).

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-88d8fc64b40b444897717785808670e6
Source dataset
uspto-grants-2011_12
Patent number
US08071771B2

Reaction notes

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