Ethyl Acetate → HCID 16661429, compound

HRID 1966302Notes

Reaction equation

HRID 1966302 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:34])=[C:6]([CH:33]=1)[O:7][CH2:8][C:9]1[C:18]([C:19]2[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:20]=2[O:28][CH3:29])=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11]([CH3:32])=[CH:12][C:13]([CH3:31])([CH3:30])[NH:14]2.[OH-].[Na+].C(OCC)(=O)C>C(O)C.[Zn]>[NH2:25][C:23]1[CH:22]=[CH:21][C:20]([O:28][CH3:29])=[C:19]([C:18]2[C:9]([CH2:8][O:7][C:6]3[CH:33]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[CH3:34])=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH3:31])([CH3:30])[CH:12]=[C:11]3[CH3:32])[CH:24]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 16661426HCID 16661426, compound

Product 1

HCID 16661429HCID 16661429, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-5-nitrophenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 14-48, 100.4 mg, 0.217 mmol) was dissolved in 4N aqueous NaOH solution (405 μL, 1.62 mmol)—ethanol (5 mL), and zinc (292.9 mg, 4.48 mmol) was added thereto, and then the reaction mixture was stirred at 110° C. overnight. Ethyl acetate (20 mL) was added to the reaction mixture and the unsoluble materials were filtered. After ethyl acetate (50 mL) was added to the filtrate, the whole was washed with water (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 (12.1 mg) as a yellow amorphous product. (Yield 13%)

Workup

  1. additionwas added
  2. filtrationthe unsoluble materials were filtered
  3. additionAfter ethyl acetate (50 mL) was added to the filtrate
  4. washthe whole was washed with water (100 mL) and saturated brine (50 mL) successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-49d17d2f94dd4ddd900c8e01530a37e0
Source dataset
uspto-grants-2013_04
Patent number
US08420635B2

Reaction notes

Loading…