Sodium hydride → Methyl 2-(2-oxo-1,2,3,4-tetrahydroquinolin-1-yl)acetate

HRID 1814166Notes

Reaction equation

HRID 1814166 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[NH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:19]>C1COCC1>[CH3:6][O:5][C:3](=[O:4])[CH2:2][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 64796Hydrocarbostyril

Product 1

HCID 21349898Methyl 2-(2-oxo-1,2,3,4-tetrahydroquinolin-1-yl)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl bromoacetate (5.72 g, 37.4 mmol) was slowly added to a stirred solution of sodium hydride (1.5 g, 37.4 mmol) and 3,4-dihydro-2 (1H)quinolinone (5.0 g, 34 mmol) in THF. The mixture was stirred at RT for 3 h. After removing the solvent, the residue was diluted with water and ether. The layers were separated and the aqueous layer was extracted with ether (3×50 mL). The combined organics were dried with MgSO4 and condensed to afford the desired product, compound 49A (7.06 g, 95%) as a yellow solid. MS m/z 220 (M+1). Step 2. Preparation of (6-Chlorosulfonyl-2-oxo-3,4-dihydro-2H-quinolin-1-yl) acetic acid methyl ester (Compound 49B).

Workup

  1. customAfter removing the solvent
  2. additionthe residue was diluted with water and ether
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ether (3×50 mL)
  5. dry with materialThe combined organics were dried with MgSO4 and condensed

Sources & evidence

ORD record
ord-1db8a9981b184a19bbe1d535a8e3ed33
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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