Ammonia methanol → HCID 23130428, compound

HRID 2080094Notes

Reaction equation

HRID 2080094 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[O:9][C:8]([CH:10]=O)=[CH:7][CH:6]=1.[NH3:17].CO>[Ni]>[F:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[O:9][C:8]([CH2:10][NH2:17])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 23130351HCID 23130351, compound

Product 1

HCID 23130428HCID 23130428, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a solution of 5-(2,4-difluoro-phenoxy)-furan-2-carbaldehyde (2060 mg, 9.19 mmol) in 7N ammonia/methanol solution (100 mL) was added Raney nickel (5.9 g), and the mixture was stirred for 24 hours at room temperature under hydrogen atmosphere. The reaction mixture was filtered through Celite pad, and the filtrate was concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate), and the title compound (1814 mg, 88.06 mmol, 87.7%) was obtained as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-55e5e65c21be420a83ab7aaa7b399f8b
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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