Oxalyl chloride → 4,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione

HRID 130323ノート

反応式

HRID 130323 の反応式
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[NH2:7].[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15]>>[CH3:12][O:11][C:9]1[CH:10]=[C:4]([O:3][CH3:2])[CH:5]=[C:6]2[C:8]=1[C:13](=[O:17])[C:14](=[O:15])[NH:7]2

参加物

3

反応物 2

HCID 65578Oxalyl chlorideHCID 218603Benzenamine, 3,5-dimethoxy-, hydrochloride (1:1)

生成物 1

HCID 115575224,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione収率 100%

実験手順

12 g (63 mmol) of 3,5-dimethoxyaniline hydrochloride and 20 ml (230 mol) of oxalyl chloride were stirred at 165° C. for 30 min. The excess of oxalyl chloride was distilled (the color of the reaction mixture changed from dark-red to green-yellow). The reaction mixture was cooled and methanol was added. The resulting suspension was heated then filtered, washed with methanol and dried to yield 13 g of 4,6-dimethoxyindole-2,3-dione (100% yield).

後処理

  1. distillationThe excess of oxalyl chloride was distilled (the color of the reaction mixture
  2. temperatureThe reaction mixture was cooled
  3. additionmethanol was added
  4. temperatureThe resulting suspension was heated
  5. filtrationthen filtered
  6. washwashed with methanol
  7. customdried

出典と根拠

ORDレコード
ord-37dc510889a84c359231f537edcf0396
出典データセット
uspto-grants-2008_06
特許番号
US07381730B2

反応ノート

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