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

HRID 1875048Notes

Reaction equation

HRID 1875048 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-78ebd4ad1f844df9b23675073551c2a0
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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