Sodium borohydride → Rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

HRID 2102702Notes

Reaction equation

HRID 2102702 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7](/[C:8](=[CH:14]/[C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)/[C:9](=[O:13])[NH:10]2)=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[C:9](=[O:13])[NH:10]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57507271Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one

Product 1

HCID 57507272Rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (12.4 g, 328 mmol) (Aldrich) was added in small portions to a suspension of E/Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one (25 g, 86 mmol) (from Example 30a supra) in methanol (400 mL) at such a rate that gas evolution was not too vigorous. When addition was complete, mixture was stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with another two portions of ethyl acetate. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography (ethyl acetate-dichloromethane, 1:2, V/V). The resulting yellow solid was recrystallized from ethyl acetate to give rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one as a pale yellow solid. (Yield 10 g, 40%).

Workup

  1. additionWhen addition
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted with another two portions of ethyl acetate
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (ethyl acetate-dichloromethane, 1:2, V/V)
  9. customThe resulting yellow solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1a6228c3e36843c0ba1f558d5c869a3d
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

Loading…