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

HRID 656364Notes

Reaction equation

HRID 656364 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][N:6]1[C:10]2([CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)[C:9](=[O:19])[NH:8][C:7]1=[O:20]>O>[CH3:5][N:6]1[C:10]2([CH2:11][C:12]3[C:17](=[CH:16][CH:15]=[C:14]([N+:1]([O-:4])=[O:2])[CH:13]=3)[CH2:18]2)[C:9](=[O:19])[NH:8][C:7]1=[O:20]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 18440308(+/-)-3-Methyl-spiro[imidazolidine-4,2'-indane]-2,5-dione

Product 1

HCID 18440305(+/-)-3-Methyl-5'-nitro-spiro[imidazolidine-4,2'-indane]-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To stirred fuming (90%) nitric acid (100 mL) was slowly added (±)-3-methyl-spiro[imidazolidine-4,2′-indane]-2,5-dione (4.5 g, 20.9 mmol) in portions over 30 min. The reaction mixture was diluted with H2O (200 mL) and the precipitate was collected by filtration, washed with H2O and dried in vacuo to give the title compound. MS: m/z=262 (M+1).

Workup

  1. customover 30 min
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-58babebd0eb9460292673d7b27635a89
Source dataset
uspto-grants-2011_12
Patent number
US08071770B2

Reaction notes

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