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

HRID 1788167Notes

Reaction equation

HRID 1788167 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 of intermediate 134, 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 (1 H, s), 8.18 (3 H, s), 7.36 (1 H, t, J=7.3 Hz), 6.79 (1 H, dd, J=10.8, 2.6 Hz), 6.66 (1 H, 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-3cb21c75aef64fe09cf234e29027eea8
Source dataset
uspto-grants-2009_03
Patent number
US07511037B2

Reaction notes

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