HCID 69288304, compound → HCID 21882747, compound

HRID 722068Notes

Reaction equation

HRID 722068 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:5]=[CH:4][N:3]=1>CO.[Pd]>[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 69288304HCID 69288304, compound

Product 1

HCID 21882747HCID 21882747, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.52 g of 2-amino-4-(2-p-tolyl-ethenyl)-3-nitropyridine (starting material N2) are dissolved in 30 ml of methanol and, after addition of 0.25 g of 10% strength palladium on carbon, are hydrogenated at 45° C. for 17 hours. The catalyst is filtered off, the filtrate is evaporated to dryness and the residue is chromatographed on a silica gel column (dichloromethane/methanol 25:1+1% triethylamine). Concentration of the pure fractions and drying in vacuo gives 0.80 g of the title compound as a brownish solid of m.p. 119–121° C. The mass spectrum shows the molecular peak MH+ at 228.2 Da.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated to dryness
  3. customthe residue is chromatographed on a silica gel column (dichloromethane/methanol 25:1+1% triethylamine)
  4. customConcentration of the pure fractions and drying in vacuo

Sources & evidence

ORD record
ord-215e75d9c81a4abfae218bf174871aba
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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