Sodium hydride → HCID 68590745, compound

HRID 1845924Notes

Reaction equation

HRID 1845924 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[O:20][CH3:21])[NH:16][C:15](=[O:22])[CH2:14][CH2:13]3)=[CH:6][CH:5]=1.Br[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[O:20][CH3:21])[N:16]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:15](=[O:22])[CH2:14][CH2:13]3)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 593166146-(4-Chlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone

Product 1

HCID 68590745HCID 68590745, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a mixture of 95% dry sodium hydride (24 mg, 1.00 mmol) in anhydrous N,N-dimethylformamide (8 mL) at room temperature was added a solution of 6-(4-chlorophenyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one (7) (110 mg, 0.38 mmol) in N,N-dimethylformamide. The reaction mixture was stirred for 30 minutes under an atmosphere of dry N2, followed by addition of a solution of tert-butyl bromoacetate (390 mg, 2.00 mmol) in N,N-dimethylformamide (2 mL). The reaction mixture was stirred at room temperature until majority of the starting material was converted (as shown by LCMS), then it was quenched by addition of methanol (10 mL). The mixture was concentrated under reduced pressure, anhydrous toluene (10 mL) was added to the residue, and the solvent removed under reduced pressure, to afford crude (tert-butyl 2-(6-(4-chlorophenyl)-7-methoxy-2-oxo-3,4-dihydroquinolin-1 (2H)-yl)acetate).

Workup

  1. stirringThe reaction mixture was stirred at room temperature until majority of the starting material
  2. customit was quenched by addition of methanol (10 mL)
  3. concentrationThe mixture was concentrated under reduced pressure, anhydrous toluene (10 mL)
  4. additionwas added to the residue
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-8fda1433903f4f0b85c0f77e855370d7
Source dataset
uspto-grants-2015_02
Patent number
US08952007B2

Reaction notes

Loading…