Hydrochloric Acid → 2-(Aminomethyl)-5-fluorophenol hydrochloride

HRID 1664172Notes

Reaction equation

HRID 1664172 reaction equation
C([O:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])C1C=CC=CC=1.[ClH:18]>C(O)C.C(OCC)(=O)C.[Pd]>[ClH:18].[OH:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[CH2:11][NH2:12]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 210698282-(Benzyloxy)-4-fluorobenzonitrile

Product 1

HCID 210698432-(Aminomethyl)-5-fluorophenol hydrochlorideYield 74.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution 2-(benzyloxy)-4-fluorobenzonitrile, (9.03 g, 39.7 mmol) in ethanol (100 mL) and ethyl acetate (100 mL) was stirred with 10% palladium on carbon (1.67 g,) and concentrated hydrochloric acid (12 mL, 144 mmol) under a hydrogen atmosphere (60 psi) for four days. The catalyst was removed by filtration through Celite®, and the filtrate was concentrated. The crude product was triturated with ether and the resulting solid collected by filtration to give the title compound (5.24 g, 74% yield) as a pale orange solid. 1H NMR (500 MHz, DMSO-D6) δ ppm: 10.81 (1H, s), 8.18 (3H, s), 7.36 (1 H, t, J=7.3 Hz), 6.79 (1H, dd, J=10.8, 2.6 Hz), 6.66 (1H, dt, J=8.5, 2.3 Hz), 3.90 (2 H, d, J=5.2 Hz).

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was triturated with ether
  4. filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record
ord-9611e3c791bd41c09db3c959ea4f9771
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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