Hydrochloric Acid → 5-Bromo-7-nitroindoline

HRID 964202

反応式

HRID 964202 の反応式
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:16])=[CH:10][C:11]=2[N+:13]([O-:15])=[O:14])[CH2:6][CH2:5]1)(=O)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Br:16][C:9]1[CH:8]=[C:7]2[C:12](=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=1)[NH:4][CH2:5][CH2:6]2

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27292431-Acetyl-5-bromo-7-nitroindoline

生成物 1

HCID 30189115-Bromo-7-nitroindoline収率 96%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

1-Acetyl-5-bromo-7-nitroindoline (5.05 g, 17.7 mmol) was added to a mixture comprising 6 ml of ethanol and 40 ml of 6N hydrochloric acid. The obtained mixture was heated under reflux for 3 hours, neutralized with sodium carbonate and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 4.13 g of 5-bromo-7-nitroindoline. This compound (301 mg, 1.24 mmol) was added to 10 ml of toluene, followed by the addition of 580 mg (2.55 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The obtained mixture was refluxed by heating under stirring for 3.5 hours and filtered to remove insolubles. The filtrate was concentrated and the obtained residue was purified by silica gel column chromatography to give 252 mg of the title compound.

後処理

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-406f0a460fd24f66be3c336cca7bcce3
出典データセット
uspto-grants-1998_06
特許番号
US05767283

関連ノート

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