Ammonia → HCID 68829511, compound

HRID 1986442Notes

Reaction equation

HRID 1986442 reaction equation
[CH2:1]([C:5]1[C:14]([C:15]#[N:16])=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:23][CH3:24])[CH:11]=2)[N:6]=1)[CH:2]([CH3:4])[CH3:3].N.O1CCCC1>[Ni].CO>[CH2:1]([C:5]1[C:14]([CH2:15][NH2:16])=[C:13]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:23][CH3:24])[CH:11]=2)[N:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 68829521HCID 68829521, compound

Product 1

HCID 68829511HCID 68829511, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 2-isobutyl-6-methoxy-4-phenylquinoline-3-carbonitrile (1.00 g, 3.16 mmol), 25% aqueous ammonia (4 ml), tetrahydrofuran (30 ml) and methanol (50 ml) was added Raney-nickel (1 ml) and the mixture was stirred under a hydrogen atmosphere at 0.5 MPa, room temperature for 6 hrs. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallized from n-hexane-ethyl acetate to give the title compound (0.44 g, yield 44%) as colorless crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography
  4. customrecrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-7dc1fc1682274ccc8ec3a21c40b6d866
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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