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

HRID 1297583Notes

Reaction equation

HRID 1297583 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].[H][H]>[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 220584394-(Aminomethyl)-3-fluorophenol hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

2-Fluoro-4-hydroxybenzonitrile (10 g, Allied Signal) was added to a 500 mL Parr flask, followed by palladium hydroxide (5 g). Anhydrous ethanol (200 mL) was then added under nitrogen atmosphere, followed by aq. concentrated hydrochloric acid (7.55 mL). The mixture was shaken under 50 psi of hydrogen for 1.5 h, then filtered through nylon. The filtrate was concentrated, washed with ethyl acetate, then dried in vacuo to yield the crude title compound (9.8 g).

Workup

  1. filtrationfiltered through nylon
  2. concentrationThe filtrate was concentrated
  3. washwashed with ethyl acetate
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8f0497613f4642f8879da6d9f710de26
Source dataset
uspto-grants-2007_07
Patent number
US07250518B2

Reaction notes

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