Ammonia methanol → HCID 58387909, compound

HRID 2080087Notes

Reaction equation

HRID 2080087 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7]1.[NH3:16].CO>[Ni]>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:16])=[CH:7]1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 23130434HCID 23130434, compound

Product 1

HCID 58387909HCID 58387909, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

7N Ammonia/methanol (40 mL) and Raney nickel (2 g) were added to 1-(3-fluoro-benzyl)-1H-pyrrole-3-carbaldehyde described in Preparation Example 58 (1.0 g, 4.9 mmol), and the solution was stirred for 18 hours under hydrogen atmosphere at room temperature. The catalyst was removed by filtering through Celite pad, then, NH silica gel was added to the filtrate, the solvent was evaporated in vacuo for adsorption, purification by NH silica gel column chromatography (hexane:ethyl acetate=2:1, then 1:1, then ethyl acetate) was carried out, and the title compound (530 mg, 2.5 mmol, 53.0%) was obtained as a brown oil.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through Celite pad
  3. additionNH silica gel was added to the filtrate
  4. customthe solvent was evaporated in vacuo for adsorption, purification by NH silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-e63eacea72d244ea867f5beb7a9b4949
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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