HCID 19603401, compound → HCID 19603330, compound

HRID 889221Notes

Reaction equation

HRID 889221 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])C1C=CC=CC=1>CCO.O1CCOCC1.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 1

HCID 19603401HCID 19603401, compound

Product 1

HCID 19603330HCID 19603330, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22560076Dioxan ethanolSolvent

Procedure

To a mixture of give 8-(benzyloxy)-2-methylquinolin-4-ol (2.34 g, 8.83 mmol) and potassium carbonate (1.83 g, 13.2 mmol) in anhydrous DMF (50 mL) was added ethyl bromoacetate (1.77 g, 10.6 mmol) with stirring under nitrogen. The mixture was heated at 80° C. for 1 h, cooled, mixed with a saturated aqueous sodium bicarbonate and extracted with EtOAc. Evaporation gave a crude product that was dissolved in dichloromethane and precipitated by the addition of a mixture of Hex/EtOAc (10/1). The precipitate was filtered and dried to give ethyl 2-((8-(benzyloxy)-2-methylquinolin-4-yl)oxy)acetate (2.13 g, 69%). A mixture of ethyl 2-((8-(benzyloxy)-2-methylquinolin-4-yl)oxy)acetate (0.70 g, 1.99 mmol), Pd/C (10%, 0.07 g) in EtOH/dioxane (20 mL/20 mL) was placed under hydrogen atmosphere with stirring overnight. The mixture was filtered and evaporated to give ethyl 2-((8-hydroxy-2-methylquinolin-4-yl)oxy)acetate (0.24 g, 46%).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-dab3146a30e141b6943b01396388e2d6
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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