Hydrochloric Acid → 5-Chloro-3-hydroxy-3-(2-methoxy-6-methylphenyl)-1,3-dihydro-2H-indol-2-one

HRID 31351

Reaction equation

HRID 31351 reaction equation
[Mg:1].[Br:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[O:10][CH3:11].[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[C:16]2=[O:23].Cl.C1[CH2:29][O:28]CC1>>[CH3:29][O:28][C:13]1[CH:21]=[CH:20][CH:19]=[C:15]([CH3:16])[C:14]=1[Mg:1][Br:2].[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[C:16]2([OH:23])[C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[O:10][CH3:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran3×HCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224MagnesiumHCID 117902332-Bromo-3-methoxytoluene

Product 2

HCID 225609215-Chloro-3-hydroxy-3-(2-methoxy-6-methylphenyl)-1,3-dihydro-2H-indol-2-oneHCID 178489966HCID 178489966, compound

Procedure

A solution of 2-methoxy-6-methylphenyl-magnesium bromide is prepared starting with 2.2 g of magnesium in 10 ml of THF and a solution of 16 g of 1-bromo-2-methoxy-6-methylbenzene in 40 ml of THF. This solution is added dropwise at RT to a mixture of 6 g of 5-chloro-1H-indole-2,3-dione in 50 ml of THF and the resulting mixture is then refluxed for 1 hour. After cooling to RT, the reaction mixture is poured into 200 ml of 3N HCl solution and extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. 5.7 g of the expected product are obtained after crystallization from iso ether.

Workup

  1. temperaturethe resulting mixture is then refluxed for 1 hour
  2. extractionextracted with EtOAc
  3. washthe organic phase is washed with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-17e7d9b1df4c454297e9cd3442b4d85f
Source dataset
uspto-grants-2008_09
Patent number
US07425566B2

Linked notes

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