3-Methyl-2-butanone → 2,3,3-Trimethyl-4,6-dicarboxy-3H-indole

HRID 2170286

反応式

HRID 2170286 の反応式
[NH:1]([C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[C:7]([C:9]([OH:11])=[O:10])[CH:8]=1)N.[CH:15]([C:18]([CH3:20])=O)([CH3:17])[CH3:16]>C(O)(=O)C>[CH3:20][C:18]1[C:15]([CH3:17])([CH3:16])[C:4]2[C:3](=[CH:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][C:5]=2[C:12]([OH:14])=[O:13])[N:1]=1

参加物

4

反応物 2

HCID 112513-Methyl-2-butanoneHCID 27723645-Hydrazinylbenzene-1,3-dicarboxylic acid

生成物 1

HCID 666034172,3,3-Trimethyl-4,6-dicarboxy-3H-indole収率 95.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of 5-hydrazinylbenzene-1.3-dicarboxylic acid (30.0 g, 129 mmol), isopropylmethylketone (22.0 mL, 205 mmol) in acetic acid (300 mL) and was heated under reflux in an oil bath for 18 h. After cooling to ambient temperature the solvent was evaporated off under reduced pressure to a small volume of ˜100 mL. To the crude mixture was added iPrOH (200 mL) and the solid was collected with a filter funnel, washed with EtOAc (3×200 mL) and ethyl ether (2×200 mL) and dried. Further drying of the solid in an oven at 50° C. under high vacuum for 18 h provided 30.44 g (95.5%) of the product.

後処理

  1. temperatureunder reflux in an oil bath for 18 h
  2. customwas evaporated off under reduced pressure to a small volume of ˜100 mL
  3. additionTo the crude mixture was added iPrOH (200 mL)
  4. customthe solid was collected with a filter funnel
  5. washwashed with EtOAc (3×200 mL) and ethyl ether (2×200 mL)
  6. customdried
  7. customFurther drying of the solid in an oven at 50° C. under high vacuum for 18 h

出典と根拠

ORDレコード
ord-6ba9665a2fb24ac3b838f1ebcdd72761
出典データセット
uspto-grants-2015_06
特許番号
US09051263B2

関連ノート

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