3-Fluoroaniline → HCID 784423, compound

HRID 600845Notes

Reaction equation

HRID 600845 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]=O)=[CH:7][CH:8]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15].[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[F:11][C:12]1[CH:13]=[C:14]([NH:15][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 97423-FluoroanilineHCID 312444-MethoxybenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 784423HCID 784423, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of anisaldehyde (0.30 ml) at r.t. in methanol (15 ml) under an argon atmosphere were added 3-fluoroaniline (0.22 ml), ZnCl2 (1.21 g) and NaBH3CN (0.43 g). The mixture was stirred at 40° C. for 1 h, then cooled to r.t. and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient:heptane->heptane/EtOAc 7:3) to give (3-fluoro-phenyl)-(4-methoxy-benzyl)-amine (617 mg) as a light yellow oil. MS (ISP): 232.1 ([M+H]+)

Workup

  1. temperaturecooled to r.t.
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography (SiO2; gradient:heptane->heptane/EtOAc 7:3)

Sources & evidence

ORD record
ord-ed76202be8d54a59944c7f6ed2fe0ae1
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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