2-Admantyl-4-methyl-5-nitrophenol → 2-Admantyl-4-methyl-5-aminophenol

HRID 2189613Notes

Reaction equation

HRID 2189613 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([N+:18]([O-])=O)=[CH:13][C:12]=1[OH:21])[CH2:8]2>CCO.[Pd]>[CH:3]12[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8][CH:1]([CH2:10]3)[CH:2]1[C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([NH2:18])=[CH:13][C:12]=1[OH:21])[CH2:9]2

Participants

4

Reactant 1

HCID 666858672-Admantyl-4-methyl-5-nitrophenol

Product 1

HCID 666858602-Admantyl-4-methyl-5-aminophenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-admantyl-4-methyl-5-nitrophenol (231 mg, 1.6 mmol) in EtOH (2 mL) was added Pd-5% wt on carbon (10 mg). The mixture was stirred under H2 (1 atm) overnight and then filtered through Celite. The filtrate was evaporated to dryness to provide 2-admantyl-4-methyl-5-aminophenol (C-12), which was used without further purification. HPLC ret. time 2.52 min, 10-99% CH3CN, 5 min run; ESI-MS 258.3 m/z (MH+).

Workup

  1. filtrationfiltered through Celite
  2. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-677e440dc106478685d86411484f2ee9
Source dataset
uspto-grants-2012_12
Patent number
US08324242B2

Reaction notes

Loading…