Ethyl Acetate → HCID 58026993, compound

HRID 1966300Notes

Reaction equation

HRID 1966300 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:29][C:30]([O:32]C)=[O:31])=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH3:19])([CH3:18])[CH:12]=[C:11]3[CH3:20])=[C:4]([O:34][CH3:35])[CH:3]=1.C(OCC)(=O)C>CO.O1CCCC1.[OH-].[Na+]>[C:30]([CH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[O:22][CH2:21][C:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[O:34][CH3:35])=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11]([CH3:20])=[CH:12][C:13]([CH3:18])([CH3:19])[NH:14]2)([OH:32])=[O:31]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 580269076-(4-Fluoro-2-methoxyphenyl)-5-(2-methoxycarbonylmethylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Product 1

HCID 58026993HCID 58026993, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

6-(4-Fluoro-2-methoxyphenyl)-5-(2-methoxycarbonylmethylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 14-1, 84.0 mg, 0.18 mmol) was dissolved in methanol (2 mL)—tetrahydrofuran mL) and 1N aqueous NaOH solution (0.56 mL) was added thereto and the mixture was stirred at room temperature overnight. After ethyl acetate (100 mL) was added to the reaction mixture, the whole was washed with 0.01N aqueous HCl solution (100 mL) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (74.1 mg) as a colorless solid. (Yield 89%)

Workup

  1. additionwas added
  2. washthe whole was washed with 0.01N aqueous HCl solution (100 mL) and saturated brine (50 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2c6737acea304a8987036de0c07b807f
Source dataset
uspto-grants-2013_04
Patent number
US08420635B2

Reaction notes

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