Diethyl Ether → HCID 19076469, compound

HRID 234481Notes

Reaction equation

HRID 234481 reaction equation
[Mg:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9].CCOCC.[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[C:19]2=[O:26]>O.C1COCC1>[CH3:19][C:18]1[CH:22]=[CH:23][CH:24]=[CH:16][C:17]=1[Mg:1][Br:2].[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[C:19]2([OH:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 72362-BromotolueneHCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium2×

Product 2

HCID 19076469HCID 19076469, compoundYield 126.4%HCID 178424303HCID 178424303, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methylphenylmagnesium bromide is prepared from 2.7 g of magnesium, 19 g of 1-bromo-2-methylbenzene and 100 ml of ether. A mixture of 5.04 g of 5-chloroisatin and 100 ml of THF is cooled in an ice bath under an argon atmosphere and the solution of magnesium compound prepared above is added slowly. After stirring for 4 hours, water is added and the solvents are evaporated off under vacuum. The residue is extracted with AcOEt, the precipitate formed is filtered off and the organic phase of the filtrate is dried over magnesium sulfate and evaporated under vacuum. The residue obtained, combined with the precipitate previously filtered off, is crystallized from MeOH to give 4.8 g of the expected product.

Workup

  1. temperatureis cooled in an ice bath under an argon atmosphere
  2. additionabove is added slowly
  3. customthe solvents are evaporated off under vacuum
  4. extractionThe residue is extracted with AcOEt
  5. customthe precipitate formed
  6. filtrationis filtered off
  7. dry with materialthe organic phase of the filtrate is dried over magnesium sulfate
  8. customevaporated under vacuum
  9. customThe residue obtained
  10. filtrationpreviously filtered off
  11. customis crystallized from MeOH

Sources & evidence

ORD record
ord-e1ae98286b044cde9273620f49baa006
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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