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

HRID 31351
ノート
印刷プレビュー

反応式

HRID 31351 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

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

生成物 2

HCID 225609215-Chloro-3-hydroxy-3-(2-methoxy-6-methylphenyl)-1,3-dihydro-2H-indol-2-one
HCID 178489966
HCID 178489966、化合物

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-17e7d9b1df4c454297e9cd3442b4d85f
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07425566B2

反応ノート

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