Potassium bisulfate → 3-[1-Methoxy-1-(4-methoxyphenyl)-methylidene]-5-nitro-2-indolinone

HRID 24954ノート

反応式

HRID 24954 の反応式
[CH3:1][O:2][CH:3](P(=O)(OCC)OCC)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.CC(C)([O-])C.[K+].[N+:26]([C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](=[O:38])[C:32]2=O)([O-:28])=[O:27].S([O-])(O)(=O)=O.[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[C:32]1[C:31]2[C:35](=[CH:36][CH:37]=[C:29]([N+:26]([O-:28])=[O:27])[CH:30]=2)[NH:34][C:33]1=[O:38])[C:4]1[CH:5]=[CH:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 516920Potassium bisulfateHCID 46692505-NitroisatinHCID 13262832Diethyl [methoxy(4-methoxyphenyl)methyl]phosphonateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 697431303-[1-Methoxy-1-(4-methoxyphenyl)-methylidene]-5-nitro-2-indolinone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
-10 °C

実験手順

6.3 g (22 mmol) of diethyl [methoxy-(4-methoxyphenyl)-methyl]-phosphonate are dissolved in 40 ml of DMF under a nitrogen atmosphere. 5.1 g (45 mmol) of potassium tert.butoxide are added batchwise at −40° C. and the mixture is then stirred for another 30 minutes at −10° C. Then 3.84 g (20 mmol) of 5-nitroisatine are added. The mixture is stirred for 1 hour at ambient temperature and then poured onto ice water containing 20 ml of saturated potassium hydrogen sulphate solution. The precipitate is suction filtered and chromatographed over silica gel (dichloromethane/methanol=10:1).

後処理

  1. stirringThe mixture is stirred for 1 hour at ambient temperature
  2. filtrationfiltered
  3. customchromatographed over silica gel (dichloromethane/methanol=10:1)

出典と根拠

ORDレコード
ord-5dd6cf5d6cb6465cb4268efc2dd2b3be
出典データセット
uspto-grants-2005_02
特許番号
US06855710B2

反応ノート

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