Sodium Hydroxide → HCID 57987619, compound

HRID 1869800Notes

Reaction equation

HRID 1869800 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:19]=[C:20]([OH:25])[C:21]([O:23][CH3:24])=[O:22])[CH:15]=2)[N:10]=1.[BH4-].[Na+].C([O-])(O)=O.[Na+].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH:20]([OH:25])[C:21]([O:23][CH3:24])=[O:22])[CH:15]=2)[N:10]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 68592948HCID 68592948, compound

Product 1

HCID 57987619HCID 57987619, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-hydroxy-2-propenoate 23 (0.38 g) in CH3OH (2 ml) is added, at 0° C., NaBH4 (36 mg). The solution is stirred for 5 h. A saturated solution of NaHCO3 and then, a solution of 1 N NaOH are added until pH=11. The aqueous phase is extracted with AcOEt (3×10 ml). The organic phases are washed with brine, dried over MgSO4 and concentrated. The residue is purified over silica gel using AcOEt/petroleum ether 30/70 then 35/65 as eluent to give methyl 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-hydroxypropanoate 55.

Workup

  1. extractionThe aqueous phase is extracted with AcOEt (3×10 ml)
  2. washThe organic phases are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified over silica gel

Sources & evidence

ORD record
ord-4883d8c4c5554a698b1bf731186b8bc9
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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