Methanol → HCID 23130560, compound

HRID 2080081Notes

Reaction equation

HRID 2080081 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][C:6]1[S:10][C:9]([CH:11]=O)=[CH:8][CH:7]=1.C(OCC)(=O)C.CO.[NH3:24].CO>[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][C:6]1[S:10][C:9]([CH2:11][NH2:24])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 21705897Ammonia methanolHCID 23130410HCID 23130410, compound

Product 1

HCID 23130560HCID 23130560, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a solution of 5-(3-chloro-benzyl)thiophene-2-carbaldehyde described in Preparation Example 44 (1.2 g, 5.08 mmol) in 7N ammonia/methanol (40 mL) was added Raney nickel (2 g), and the solution was stirred at room temperature for 17 hours under hydrogen atmosphere. The reaction solution was filtered through Celite pad, the catalyst was removed, then, this filtrate was evaporated in vacuo, the residue was purified by silica gel column chromatography (ethyl acetate, then ethyl acetate:methanol=5:1), and the title compound (740 mg, 3.12 mmol, 61.4%) was obtained as a brown oil.

Workup

  1. filtrationThe reaction solution was filtered through Celite pad
  2. customthe catalyst was removed
  3. customthis filtrate was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-c9d0f2786ed246058a3d1f434c89c620
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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