HCID 11961865, compound → HCID 14010516, compound

HRID 2203266Notes

Reaction equation

HRID 2203266 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:13][N+:14]([O-])=O)[CH2:9][N+:10]([O-])=O)=[CH:4][CH:3]=1.[H][H]>CO.[Pt](=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:13][NH2:14])[CH2:9][NH2:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11961865HCID 11961865, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14010516HCID 14010516, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

According to the procedure described in Eur. J. Org. Chem. 2010, 3, 484-493, a mixture of 1-chloro-4-[2-nitro-1-(nitromethyl)ethyl]benzene (80 mg, 0.327 mmol) and 18 mg platinum (IV) oxide in 5 mL MeOH contained in a pressure tube was reacted under 50 PSI hydrogen. After 15 hours the mixture was filtered through Celite, rinsed with MeOH and evaporated to give a quantitative yield (60 mg) of the title compound as a yellow-orange oil. 1H NMR (CD3OD) δ: 7.34-7.38 (m, 2H), 7.21-7.29 (m, 2H), 2.88-2.98 (m, 2H), 2.73-2.86 (m, 3H).

Workup

  1. customcontained in a pressure tube
  2. filtrationAfter 15 hours the mixture was filtered through Celite
  3. washrinsed with MeOH
  4. customevaporated

Sources & evidence

ORD record
ord-1c4d42e5def84ff689948f39ee50d5f4
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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