Diethyl Ether → 5-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-one

HRID 1243315Notes

Reaction equation

HRID 1243315 reaction equation
[Mg:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[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-].CC[O:27][CH2:28]C>C1COCC1>[CH3:28][O:27][C:12]1[CH:13]=[CH:14][CH:18]=[CH:19][C:20]=1[Mg:1][Br:2].[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]=[CH:5][C:4]=1[O:9][CH3:10]

Participants

8

Reactant 5

HCID 3283Diethyl Ether2×HCID 113582-BromoanisoleHCID 25517Ammonium ChlorideHCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium

Product 2

HCID 219059555-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-oneHCID 178489560HCID 178489560, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound is prepared according to the procedure described in WO 95/18105. A solution of 2-methoxyphenylmagnesium bromide is prepared from 16 g of magnesium in 35 ml of ether and a solution of 124 g of 1-bromo-2-methoxybenzene in 175 ml of ether. This solution is added dropwise, under an argon atmosphere, to a mixture of 30 g of 5-chloro-1H-indole-2,3-dione in 250 ml of THF, cooled beforehand in an icebath, and the mixture is then left stirring and the temperature is allowed to return to RT. After stirring for 1 hour at RT, the reaction mixture is poured slowly into saturated NH4Cl solution and the THF is evaporated off under vacuum. The precipitate formed is filtered off by suction and washed with iso ether. 42 g of the expected product are obtained, and are used without further purification in the following step.

Workup

  1. customThis compound is prepared
  2. temperaturecooled
  3. waitthe mixture is then left
  4. customto return to RT
  5. stirringAfter stirring for 1 hour at RT
  6. customthe THF is evaporated off under vacuum
  7. customThe precipitate formed
  8. filtrationis filtered off by suction
  9. washwashed with iso ether

Sources & evidence

ORD record
ord-448287515a8c4392a64d43c46f599c9e
Source dataset
uspto-grants-2006_10
Patent number
US07119086B2

Reaction notes

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