Hydrochloric Acid → 3-(1-Aminoethyl)phenol

HRID 449519Notes

Reaction equation

HRID 449519 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[N:10]O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.Cl.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>CO.[Pd]>[NH2:10][CH:8]([C:4]1[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=1)[CH3:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 441036D-PsicoseHCID 727653751-(3-Hydroxyphenyl)ethanone oxime

Product 1

HCID 123479863-(1-Aminoethyl)phenolYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(3-Hydroxyphenyl)ethanone oxime (1.2 g; 7.9 mmol) was dissolved in methanol (20 mL), degassed with nitrogen. 10% Palladium on carbon (0.1 g) and conc. HCl (100 uL, 3 mmol) were added. The reaction was shaken under Parr shaker at 50 Psi for 5 h. The reaction was filtered and concentrated under reduced pressure to give crude 3-(1-aminoethyl)phenol (1.0 g, 100%) as a yellow oil. Analytical LCMS (M+H)+: m/z=138.0.

Workup

  1. customdegassed with nitrogen
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dfb2b103b7cb4dc7b1ca00f5c76ab589
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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