HCID 67513886, compound → HCID 67513794, compound

HRID 1508521Notes

Reaction equation

HRID 1508521 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[CH3:19])=[CH:5][C:4]=1[N+:20]([O-])=O)=[CH2:2]>[Pd].CO>[NH2:20][C:4]1[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[CH3:19])[CH:7]=[CH:8][C:3]=1[CH2:1][CH3:2]

Participants

4

Reactant 1

HCID 67513886HCID 67513886, compound

Product 1

HCID 67513794HCID 67513794, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 4′-ethenyl-2-methyl-3′-nitrobiphenyl-4-carboxylate (1.6206 g, 5.45 mmol), palladium on carbon (0.290 g, 0.273 mmol) and MeOH (50 mL) were stirred under a balloon atmosphere of H2 at room temperature overnight. The reaction crude was filtered and concentrated in vacuo to afford a light yellow oil. The resulting oil was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel 100 g cartridge). The column was eluted by an EtOAc/hexanes mixture (0% to 40%). Related fractions were pooled and evaporated to afford a light yellow oil as the titled compound. LCMS calc.=269.14. found=270.30 (M+H)+.

Workup

  1. customThe reaction crude
  2. filtrationwas filtered
  3. concentrationconcentrated in vacuo
  4. customto afford a light yellow oil
  5. customThe resulting oil was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel 100 g cartridge)
  6. washThe column was eluted by an EtOAc/hexanes mixture (0% to 40%)
  7. customevaporated

Sources & evidence

ORD record
ord-af4bc8b846eb4b0d93a845c5a29b623d
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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