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

HRID 1372273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372273
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]

Komponenten

6

Edukt 2

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

Produkt 1

HCID 210698432-(Aminomethyl)-5-fluorophenol hydrochlorideAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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 (1H, s), 8.18 (3H, s), 7.36 (1H, 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 (2H, d, J=5.2 Hz).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8ccc5eb04d7443c085203606fa80cebc
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157447B2

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