Benzene, 1-nitro-3-[2-nitro-1-(nitromethyl)ethyl]- → HCID 86702440, compound

HRID 2203269Notes

Reaction equation

HRID 2203269 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH2:15][N+:16]([O-])=O)[CH2:11][N+:12]([O-])=O)[CH:5]=1)([O-])=O.[H][H]>CO.[Pt](=O)=O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]([CH2:15][NH2:16])[CH2:11][NH2:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 11230571Benzene, 1-nitro-3-[2-nitro-1-(nitromethyl)ethyl]-HCID 178418361HCID 178418361, compound

Product 1

HCID 86702440HCID 86702440, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-nitro-3-[2-nitro-1-(nitromethyl)ethyl]benzene (115 mg, 0.45 mmol) and 58 mg platinum (IV) oxide in 6 mL MeOH contained in a pressure tube was reacted under 65 PSI hydrogen. After 16 hours the mixture was filtered and rinsed with MeOH. The MeOH solution of product was stored under N2 in the freezer and used as is for the next reaction [upon evaporation of MeOH solvent 69.9 mg (94%) of the title compound was obtained as a light yellow oil]. 1H NMR (CD3OD) δ: 7.06-7.13 (m, 1H), 6.55-6.65 (m, 3H), 2.83-2.91 (m, 2H), 2.72-2.81 (m, 2H), 2.57-2.68 (m, 1H).

Workup

  1. customcontained in a pressure tube
  2. filtrationAfter 16 hours the mixture was filtered
  3. washrinsed with MeOH
  4. customas is for the next reaction [
  5. customupon evaporation of MeOH solvent 69.9 mg (94%) of the title compound
  6. customwas obtained as a light yellow oil]

Sources & evidence

ORD record
ord-0a7ef9ce788a494b820565998c7a6626
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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