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Tetrahydrofuran → 5-Chloro-3-hydroxy-3-(3-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

HRID 31344
Notes
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Reaction equation

HRID 31344 reaction equation
[Mg:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2=[O:22].[NH4+].[Cl-].C1[CH2:29][O:28]CC1>>[CH3:29][O:28][C:18]1[CH:19]=[C:20]([Mg:1][Br:2])[CH:12]=[CH:13][CH:14]=1.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2([OH:22])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran3×HCID 169713-BromoanisoleHCID 25517Ammonium ChlorideHCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium

Product 2

HCID 225608255-Chloro-3-hydroxy-3-(3-methoxyphenyl)-1,3-dihydro-2H-indol-2-one
HCID 178490745
HCID 178490745, compound

Procedure

A solution of 3-methoxyphenylmagnesium bromide is prepared from 3.5 g of magnesium in 10 ml of THF and from a solution of 25 g of 1-bromo-3-methoxy-benzene in 40 ml of THF. This solution is added dropwise, under a nitrogen atmosphere, to a mixture of 8 g of 5-chloro-1H-indole-2,3-dione in 50 ml of THF, while keeping the temperature of the reaction medium below 40° C., followed by refluxing for 1 hour. The reaction mixture is cooled to RT, poured into saturated NH4Cl solution and extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. 9.1 g of the expected product are obtained after crystallization from hot iso ether; m.p.=212° C.

Workup

  1. customthe temperature of the reaction medium below 40° C.
  2. temperatureby refluxing for 1 hour
  3. extractionextracted with EtOAc
  4. washthe organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-1935a5b414384453ae3b0fd32dff8349
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425566B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes