Hydrochloric Acid → 4-(Aminomethyl)-3-fluorophenol hydrochloride

HRID 1828838Notes

Reaction equation

HRID 1828838 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[ClH:11]>[OH-].[Pd+2].[OH-].C(O)C>[ClH:11].[NH2:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 220584394-(Aminomethyl)-3-fluorophenol hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-fluoro-4-hydroxy-benzonitrile (6 g, 43.8 mmol), palladium hydroxide (600 mg), ethanol (60 ml) and 2N hydrochloric acid (6 ml) was hydrogenated (60 psi) for 18 hours. The mixture was filtered through Arbocel® and the filter cake was washed with methanol and the filtrates were evaporated in-vacuo. The residue was triturated with diethylether to give 4-aminomethyl-3-fluoro phenol hydrochloride (4.71 g).

Workup

  1. customfor 18 hours
  2. filtrationThe mixture was filtered through Arbocel®
  3. washthe filter cake was washed with methanol
  4. customthe filtrates were evaporated in-vacuo
  5. customThe residue was triturated with diethylether

Sources & evidence

ORD record
ord-244b95a43b1748218f7ee689e02ae896
Source dataset
uspto-grants-2006_06
Patent number
US07060717B2

Reaction notes

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