5-(4-Fluorophenoxy)furan-2-carbaldehyde → C-(5-(4-Fluoro-phenoxy)-furan-2-yl)methylamine

HRID 2080148Notes

Reaction equation

HRID 2080148 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[O:11][C:10]([CH:12]=O)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[NH3:16].CO>[Ni]>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[O:11][C:10]([CH2:12][NH2:16])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 110419065-(4-Fluorophenoxy)furan-2-carbaldehydeHCID 21705897Ammonia methanol

Product 1

HCID 23130578C-(5-(4-Fluoro-phenoxy)-furan-2-yl)methylamineYield 81%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A suspension of 5-(4-fluoro-phenoxy)-furan-2-carbaldehyde described in Preparation Example 168 (4.3 g, 20.9 mmol), Raney nickel (1.5 g) and 7N ammonia-methanol solution (40 mL) was stirred at room temperature for 15 hours under hydrogen atmosphere (1 atm). The reaction solution was filtered through Celite pad to remove the catalyst, and the filtrate was concentrated. The residue was dissolved in ethyl acetate, filtered by NH silica gel lined over a glass filter, and then, this filtrate was concentrated to obtain the title compound (3.5 g, 16.9 mmol, 81%).

Workup

  1. filtrationThe reaction solution was filtered through Celite pad
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. filtrationfiltered by NH silica gel
  6. filtrationfilter
  7. concentrationthis filtrate was concentrated

Sources & evidence

ORD record
ord-66a6a9f67f6d401a9c54654d1ef625cb
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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