Hydrochloric Acid → 5-Bromo-7-nitroindoline

HRID 1173101

反応式

HRID 1173101 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

5.05 g (17.7 mmol) of 1-acetyl-5-bromo-7-nitroindoline was dissolved into a mixed solution of 6 ml of ethanol and 40 ml of 6 N hydrochloric acid, followed by heating under reflux for 3 hours. After neutralizing by adding sodium carbonate thereto, the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel column chromatography, to give 4.13 g of 5-bromo-7-nitroindoline. 301 mg (1.24 mmol) of this compound was added to 10 ml of toluene, and then 580 mg (2.55 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was added thereto. After heating under reflux for 3.5 hours while stirring, the insoluble matters were filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 252 mg of the title compound.

後処理

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThen, the residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fead91756ba84e9b8e4ae62d4d3fbe5d
出典データセット
uspto-grants-2010_11
特許番号
US07834049B2

関連ノート

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