Methanol → HCID 68829612, compound

HRID 1986495Notes

Reaction equation

HRID 1986495 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:12]([C:22]#[N:23])=[C:11]2[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=O)C.CO.[OH-].[Na+].O>O1CCCC1>[OH:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:12]([C:22]#[N:23])=[C:11]2[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 68830320HCID 68830320, compound

Product 1

HCID 68829612HCID 68829612, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{[3-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}ethyl acetate (4.0 g, 9.9 mmol) in tetrahydrofuran (20 ml)-methanol (20 ml) was added 2N aqueous sodium hydroxide solution (20 ml). The obtained mixture was stirred at room temperature for 3 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to give 6-(2-hydroxyethoxy)-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (3.2 g, yield 89%) as crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-07c6b9cde4a049f880a9ecffb5af20c4
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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