tert-Butyl bromoacetate → HCID 68590745, compound

HRID 1183765Notes

Reaction equation

HRID 1183765 reaction equation
[H-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][C:18]=2[O:19][CH3:20])[NH:15][C:14](=[O:21])[CH2:13][CH2:12]3)=[CH:5][CH:4]=1.Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][C:18]=2[O:19][CH3:20])[N:15]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:14](=[O:21])[CH2:13][CH2:12]3)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 166653HydrideHCID 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 sodium0 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. additionTo a mixture of 95%
  2. stirringThe reaction mixture was stirred at room temperature until majority of the starting material
  3. customit was quenched by addition of methanol (10 mL)
  4. concentrationThe mixture was concentrated under reduced pressure, anhydrous toluene (10 mL)
  5. additionwas added to the residue
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-536c87871b9a4be38de6ad60683cf0b5
Source dataset
uspto-grants-2014_03
Patent number
US08664379B2

Reaction notes

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