Ammonia → {[4-Chloro-2-fluoro-3-(1-naphthalenyloxy)phenyl]methyl}amine

HRID 1875048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875048
Br[CH2:2][C:3]1[C:4]([F:21])=[C:5]([O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[C:6]([Cl:9])=[CH:7][CH:8]=1.[NH3:22].CO>ClCCl>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH2:22])=[C:4]([F:21])[C:5]=1[O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 887MethanolHCID 684855581-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}naphthalene

Produkt 1

HCID 68486009{[4-Chloro-2-fluoro-3-(1-naphthalenyloxy)phenyl]methyl}amineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}naphthalene (0.96 g, 2.63 mmol) in dichloromethane (10 mL) was added 7N ammonia in methanol (20 mL, 140 mmol). The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was triturated with dichloromethane to give the desired product (0.769 g, 87%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.29-8.37 (m, 1H), 7.94-8.03 (m, 1H), 7.60-7.71 (m, 4H), 7.56 (t, 1H), 7.36 (t, 1H), 6.56 (d, 1H), 4.13 (s, 2H). ES MS: m/z 302 (M+1).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was triturated with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-78ebd4ad1f844df9b23675073551c2a0
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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