Pivalaldehyde → E-6-chloro-3-(2,2-dimethyl-propylidene)-1,3-dihydro-indol-2-one

HRID 1727949Notes

Reaction equation

HRID 1727949 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH3:12][C:13]([CH3:17])([CH3:16])[CH:14]=O.N1CCCC1>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:12]\[C:13]([CH3:17])([CH3:16])[CH3:14])/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 12417PivalaldehydeHCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-one

Product 1

HCID 57565943E-6-chloro-3-(2,2-dimethyl-propylidene)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in example 1a, 6-chlorooxindole (0.88 g, 5 mmol) was reacted with 2,2-dimethyl-propionaldehyde (0.43 g, 5 mmol) (Aldrich), pyrrolidine (0.36 g, 5 mmol) in methanol to give a mixture of E- and Z-6-Chloro-3-(2,2-dimethyl-propylidene)-1,3-dihydro-indol-2-one. Purification by chromatography (EtOAc:hexanes=1:2) led to E-6-chloro-3-(2,2-dimethyl-propylidene)-1,3-dihydro-indol-2-one as an off-white foam (Yield 0.82 g, 70%).

Workup

  1. customto give
  2. customPurification by chromatography (EtOAc:hexanes=1:2)

Sources & evidence

ORD record
ord-6c311f1e01c94eba9bfa212f0f3adfd7
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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