4-Nitrobenzenebutanol → 4-(4-Aminophenyl)butan-1-OL

HRID 926819Notes

Reaction equation

HRID 926819 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 5908694-Nitrobenzenebutanol2×HCID 178418361HCID 178418361, compound

Product 1

HCID 150062264-(4-Aminophenyl)butan-1-OLYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(4-nitrophenyl)butanol (compound 19, 1.7 mL, 10.2 mmol) was dissolved in methanol (20 mL) to which 10% Palladium on carbon (0.2 g) was added and the mixture was hydrogenated using hydrogen gas (30 psi) at ambient temperature for 1 hr. The mixture was filtered through celite filter aid and solvent was evaporated from the filtrate under vacuum to give 1.3 g (77% yield) of crude product. Mass spectrum (M+H)+ calcd for C10H15NO 166.1. found 166.1.

Workup

  1. additionwas added
  2. customat ambient temperature
  3. customfor 1 hr
  4. filtrationThe mixture was filtered through celite
  5. filtrationfilter aid and solvent
  6. customwas evaporated from the filtrate under vacuum

Sources & evidence

ORD record
ord-0a28b7036b814bb5b13ae5b3e8c0ddaa
Source dataset
uspto-grants-2016_03
Patent number
US09289512B2

Reaction notes

Loading…