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

HRID 656401Notes

Reaction equation

HRID 656401 reaction equation
[CH3:1][N:2]1[C:6]2([CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=3)[CH2:7]2)[C:5](=[O:18])[NH:4][C:3]1=[O:19].[N+:20]([O-])(O)=O.OS(O)(=O)=O>>[NH2:20][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][C:11]=1[N+:15]([O-:17])=[O:16])[CH2:14][C:6]1([C:5](=[O:18])[NH:4][C:3](=[O:19])[N:2]1[CH3:1])[CH2:7]2

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 18440305(+/-)-3-Methyl-5'-nitro-spiro[imidazolidine-4,2'-indane]-2,5-dione2×

Product 1

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

Procedure

To (±)-5′-amino-3-methyl-spiro[imidazolidine-4,2′-indane]-2,5-dione (100 mg, 0.432 mmol, described in Intermediate 7) at 0° C. were added 70% HNO3 (1 mL) followed by conc. H2SO4 (1 mL). The resulting mixture was allowed to warm to ambient temperature and stirred for 18 h, then poured onto ice and the precipitate was removed by filtration. The aqueous filtrate was purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound. MS: m/z=277 (M+1).

Workup

  1. additionpoured onto ice
  2. customthe precipitate was removed by filtration
  3. customThe aqueous filtrate was purified by HPLC
  4. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-924be87e47194fe0af294cac7e0e9237
Source dataset
uspto-grants-2011_12
Patent number
US08071771B2

Reaction notes

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