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

HRID 2426165Notes

Reaction equation

HRID 2426165 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-f413015b25714b01bee4171046283fc8
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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