4-Methoxybenzylamine → HCID 18766346, compound

HRID 480965Notes

Reaction equation

HRID 480965 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1F)[C:15]#[N:16].C(=O)([O-])O.[Na+]>>[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[NH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:15]#[N:16]

Participants

4

Reactant 3

HCID 754524-MethoxybenzylamineHCID 516892Sodium BicarbonateHCID 5872033,4-Difluorobenzonitrile

Product 1

HCID 18766346HCID 18766346, compoundYield 61.2%

Conditions

Temperature
0 °C

Procedure

4-Methoxybenzylamine (5.6 ml, 43.1 mmol) was added dropwise to a solution of commercially available 3,4-difluorobenzonitrile (2.0 g, 14.4 mmol) in anhydrous di(ethylene glycol) dimethyl ether (10 ml) cooled to 0° C. with stirring. The resulting mixture was stirred at 120° C. for 1 hour. At the end of this time, the reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution at room temperature. The resulting mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Hexane was added to the crystalline residue to give 3-fluoro-4-[(4-methoxybenzyl)amino]benzonitrile (2.26 g, yield 61%) as white fluffy crystals.

Workup

  1. stirringThe resulting mixture was stirred at 120° C. for 1 hour
  2. customThe resulting mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionHexane was added to the crystalline residue

Sources & evidence

ORD record
ord-d99cdf6bc7344887bc5d07244e58bb28
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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