Ammonia methanol → HCID 57608214, compound

HRID 1171217Notes

Reaction equation

HRID 1171217 reaction equation
[NH3:1].CO.[CH:4]1([CH2:7][O:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[C:14]([CH:18]=O)[NH:15]3)=[CH:11][CH:10]=2)[CH2:6][CH2:5]1>[Ni]>[CH:4]1([CH2:7][O:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[C:14]([CH2:18][NH2:1])[NH:15]3)=[CH:11][CH:10]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 57608279HCID 57608279, compound

Product 1

HCID 57608214HCID 57608214, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To an ammonia-methanol (5 mL) solution of 6-cyclopropylmethoxy-1H-indole-2-carbaldehyde (144 mg, 669 μmol) described in Production Example 73-1-4 was added Raney nickel, which was stirred at room temperature for 8 hours under hydrogen atmosphere. The reaction mixture was filtered through Celite and the filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (91 mg, 63%) as a pale brown oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-c5736aa96f5d445abb4f09cee30b690c
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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