Ammonia methanol → HCID 23130476, compound

HRID 2080077Notes

Reaction equation

HRID 2080077 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]2[S: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]([CH2:6][C:7]2[S:11][C:10]([CH2:12][NH2:16])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 23130596HCID 23130596, compound

Product 1

HCID 23130476HCID 23130476, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

7N ammonia/methanol (30 mL) and Raney nickel (500 mg) were added to 5-(4-fluorobenzyl)thiophene-2-carbaldehyde described in Preparation Example 37 (460 mg, 2.09 mmol), and the mixture was stirred for 14 hours under hydrogen atmosphere at room temperature. The catalyst was removed by filtering through Celite pad, then, purification by silica gel column chromatography (ethyl acetate, then ethyl acetate:methanol=4:1) was carried out, and the title compound (70 mg, 0.316 mol, 15.1%) was obtained as an oil.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through Celite pad
  3. custompurification by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-afac6b83eeb247e3a9e2d7a114a3daf1
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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