HCID 86681656, compound → HCID 86681655, compound

HRID 571239Notes

Reaction equation

HRID 571239 reaction equation
Cl[C:2]1(Cl)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[N:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:3]1=[O:18]>C(O)(=O)C.[Zn]>[CH3:12][O:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:3](=[O:18])[CH2:2]2

Participants

4

Reactant 1

HCID 86681656HCID 86681656, compound

Product 1

HCID 86681655HCID 86681655, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 2-(3,3-dichloro-5-methoxy-2-oxoindolin-1-yl)acetate (1.3 g, 4.27 mmol) in acetic acid (30 ml), zinc powder (1.118 g, 17.10 mmol) was added, and the mixture was reacted at room temperature for 15 minutes; then the insoluble inorganics were filtered off and washed with MeOH. The crude title compound was obtained after evaporation under reduced pressure and used in the next step without further purification (760 mg, 3.23 mmol, 76% yield). MS/ESI+ 236.0 [MH]+.

Workup

  1. customthe mixture was reacted at room temperature for 15 minutes
  2. filtrationthen the insoluble inorganics were filtered off
  3. washwashed with MeOH

Sources & evidence

ORD record
ord-46d7b3da7cf94902bfa7cd7597670842
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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