Ethyl Acetate → 5'-Amino-1',3'-dihydro-2H,5H-spiro[imidazolidine-4,2'-indene]-2,5-dione

HRID 1175678Notes

Reaction equation

HRID 1175678 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8]1([C:16](=[O:17])[NH:15][C:14](=[O:18])[NH:13]1)[CH2:7]2)([O-])=O.CCOC(C)=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8]1([C:16](=[O:17])[NH:15][C:14](=[O:18])[NH:13]1)[CH2:7]2

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 16638331HCID 16638331, compound

Product 1

HCID 184403095'-Amino-1',3'-dihydro-2H,5H-spiro[imidazolidine-4,2'-indene]-2,5-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5′-Nitro-1′,3′-dihydrospiro[imidazolidine-4,2′-indene]-2,5-dione (10.1 mmol, 2.5 g) and 10% Pd/C (0.25 g) in 1:1 EtOAc:MeOH (300 ml) were stirred under H2 (1 atm) for 1.5 h. The solution was filtered and evaporated to give the title compound as a brown solid that was used with out further purification. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=218; tR=2.4.

Workup

  1. filtrationThe solution was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-682fddc484a04f54a5eb80610e4e6790
Source dataset
uspto-grants-2010_11
Patent number
US07842686B2

Reaction notes

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