Ammonia → HCID 86605662, compound

HRID 1986497Notes

Reaction equation

HRID 1986497 reaction equation
[C:1]([C:3]1[C:4]([CH2:32][CH:33]([CH3:35])[CH3:34])=[N:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[CH:10][C:9]([O:20][CH2:21][CH2:22][O:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:8][CH:7]=2)#[N:2].N>[Ni].CO>[NH2:2][CH2:1][C:3]1[C:4]([CH2:32][CH:33]([CH3:35])[CH3:34])=[N:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1)=[CH:10][C:9]([O:20][CH2:21][CH2:22][O:23][CH2:24][C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])=[CH:8][CH:7]=2

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86605661HCID 86605661, compound

Product 1

HCID 86605662HCID 86605662, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a mixture of tert-butyl (2-{[3-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}ethoxy)acetate (0.9 g, 1.9 mmol), 25% aqueous ammonia (5 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 5 hrs. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl (2-{[3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)-6-quinolinyl]oxy}ethoxy)acetate as an oil (0.6 g). The oil and p-toluenesulfonic acid monohydrate (0.23 g, 1.2 mmol) were dissolved in ethanol (50 ml) and concentrated under reduced pressure. The residue was crystallized from diethyl ether and recrystallized from methanol-diethyl ether to give the title compound (0.7 g, yield 58%) as 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

Sources & evidence

ORD record
ord-f4935f35dffd49a6bd5f7f9b16369bd9
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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