HCID 86681652, compound → HCID 43446487, compound

HRID 571235Notes

Reaction equation

HRID 571235 reaction equation
Cl[C:2]1(Cl)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[N:4]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:3]1=[O:19]>C(O)(=O)C.C(OCC)(=O)C.[Zn]>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:3](=[O:19])[CH2:2]2

Participants

5

Reactant 1

HCID 86681652HCID 86681652, compound

Product 1

HCID 43446487HCID 43446487, compoundYield 55.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of methyl 2-(3,3-dichloro-5-nitro-2-oxoindolin-1-yl)acetate (0.314 g, 0.984 mmol) in acetic acid (10 ml), zinc powder (0.901 g, 13.78 mmol) was added potion wise at room temperature, and the mixture was stirred for 2 hours. Then the mixture was diluted with ethyl acetate, the solid was filtered off and washed with ethyl acetate and water. The filtrate was basified with solid K2CO3 (pH=8), and the phases were separated. The aqueous phase was extracted with DCM, and the combined organic layers were dried over sodium sulfate. The solvent was removed, and the crude was purified by filtration on silica gel cartridge (DCM:EtOAc from 80:20 to 50:50) affording methyl 2-(5-amino-2-oxoindolin-1-yl)acetate (0.120 g, 0.545 mmol, 55% yield). MS/ESI+ 220.9 [MH]+.

Workup

  1. additionwas added potion wise at room temperature
  2. filtrationthe solid was filtered off
  3. washwashed with ethyl acetate and water
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with DCM
  6. dry with materialthe combined organic layers were dried over sodium sulfate
  7. customThe solvent was removed
  8. filtrationthe crude was purified by filtration on silica gel cartridge (DCM:EtOAc from 80:20 to 50:50)

Sources & evidence

ORD record
ord-0f0754a7973540ce8a1252b42c2d6a7c
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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