Dimethyl Sulfoxide → Rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

HRID 556446Notes

Reaction equation

HRID 556446 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.CS(C)=O.O>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

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 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-oneYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (3.0 g, 79 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 (19 g, 66 mmol) (from example 1a supra) in methanol (200 mL) and DMSO (50 mL) at such a rate that gas evolution was not too vigorous. When the addition was complete, mixture was stirred at room temperature for 0.5 hr-1 hr. After adding to water (200 mL), the resulting precipitate was collected and dried to give 18 g of rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one as a light yellow solid. MS: 293 (M+H)+.

Workup

  1. additionWhen the addition
  2. customthe resulting precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-5bbc96de926048c281cda0eb2d5966b7
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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