HCID 86702450, compound → HCID 86702451, compound

HRID 2203293Notes

Reaction equation

HRID 2203293 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]([CH2:13][N+:14]([O-])=O)[CH2:9][N+:10]([O-])=O)[CH:5]=[CH:4][C:3]=1[N+:17]([O-])=O>[Pt].[Pd].[Ni].CO>[NH2:17][C:3]1[CH:4]=[CH:5][C:6]([CH:8]([CH2:13][NH2:14])[CH2:9][NH2:10])=[CH:7][C:2]=1[CH3:1]

Participants

6

Reactant 1

HCID 86702450HCID 86702450, compound

Product 1

HCID 86702451HCID 86702451, compoundYield 96%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 887MethanolSolvent

Conditions

Temperature
57.5 °C

Procedure

A heavy-walled flask under N2 was charged with 10 wt % platinum on carbon (3.8 g), 10 wt % palladium on carbon (50% wet, 11.3 g), Raney Ni (wet, 11.3 g), 2-methyl-1-nitro-4-(2-nitro-1-nitromethyl-ethyl)-benzene (37.7 g, 0.14 mol), and MeOH (754 mL). After attaching the flask to the hydrogenation apparatus, it was subjected to three vacuum degas-nitrogen purge cycles, followed by three nitrogen outgas-hydrogen purge cycles. The resulting suspension was stirred under 60 psi of H2 at 55-60° C. for at least 72 h. The reaction mixture was filtered through a celite pad (27 g), rinsing with methanol (760 mL). The filtrate and rinse were concentrated to dryness in vacuo to give the crude title compound as red-brown gum (24 g, 96% yield). This material was used without further purification.

Workup

  1. customdegas-nitrogen
  2. custompurge cycles
  3. custompurge cycles
  4. filtrationThe reaction mixture was filtered through a celite pad (27 g)
  5. washrinsing with methanol (760 mL)
  6. washThe filtrate and rinse
  7. concentrationwere concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-f3f46847f73f45219bbb6e246261189a
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

Loading…