Sodium Hydroxide → HCID 68830457, compound

HRID 1986420Notes

Reaction equation

HRID 1986420 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([CH2:21][CH:22]([CH3:24])[CH3:23])=[N:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([C:19]#[N:20])=[CH:8][CH:7]=2.[OH-:25].[Na+]>CS(C)=O>[NH2:1][CH2:2][C:3]1[C:4]([CH2:21][CH:22]([CH3:24])[CH3:23])=[N:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([C:19]([NH2:20])=[O:25])=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68828575HCID 68828575, compound

Product 1

HCID 68830457HCID 68830457, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(aminomethyl)-2-isobutyl-4-phenylquinoline-6-carbonitrile (0.11 g, 0.35 mmol) in dimethyl sulfoxide (4 ml) was added 1N aqueous sodium hydroxide solution (2 ml) and the mixture was stirred at 80° C. for 3 hrs. The reaction mixture was partitioned between ethyl acetate (50 ml) and 1N aqueous sodium hydroxide solution (50 ml) and the aqueous layer was extracted 4 times with ethyl acetate (50 ml). The organic layers were combined and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by preparative HPLC. The objective fractions were combined and concentrated under reduced pressure. The residue was partitioned between ethyl acetate (25 ml)-tetrahydrofuran (25 ml) and 1N aqueous sodium hydroxide solution (25 ml). The organic layer was washed with saturated brine (10 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was crystallized from diisopropyl ether-ethyl acetate to give the title compound (0.043 g, yield 37%) as pale-yellow crystals.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (50 ml) and 1N aqueous sodium hydroxide solution (50 ml)
  2. extractionthe aqueous layer was extracted 4 times with ethyl acetate (50 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by preparative HPLC
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was partitioned between ethyl acetate (25 ml)-tetrahydrofuran (25 ml) and 1N aqueous sodium hydroxide solution (25 ml)
  8. washThe organic layer was washed with saturated brine (10 ml)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated
  11. customthe residue was crystallized from diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-23a953a3149642659638306bc74836fb
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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