Hydrochloric Acid → 5-(propan-2-yl)-1H-indole-2,3-dione

HRID 1081265ノート

反応式

HRID 1081265 の反応式
[CH3:1][CH:2]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)[CH3:3].Cl.Cl.N[OH:14].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].Cl[C:33](Cl)(Cl)[CH:34]([OH:36])O>O.C(O)C>[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:9][CH:10]=1)[NH:8][C:33](=[O:14])[C:34]2=[O:36])[CH3:3]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 74644-IsopropylanilineHCID 62649Sodium sulfate decahydrateHCID 443297Hydroxyamine hydrochloride

生成物 1

HCID 5898025-(propan-2-yl)-1H-indole-2,3-dione

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒4 回

反応条件

温度
80 °C

実験手順

4-(1-Methylethyl)-aniline (6.75 g) was dissolved in water (30 ml) containing concentrated hydrochloric acid (4.4 ml). Hydroxylamine hydrochloride (16.9 g) in water (48 ml) and sodium sulphate decahydrate (100 g) in water (120 ml) were added, followed by chloral hydrate (16.5 g) in ethanol (180 ml). The reaction mixture was heated under reflux for 3 hours, then poured into water. The solid isonitroso-acetanilide intermediate was collected by filtration, washed and dried. This material was cooled in an ice-salt bath and concentrated sulphuric acid (48 ml) was added dropwise with stirring. After addition was complete the mixture was warmed to 80° C. for 20 minutes and then poured onto crushed ice. The resulting red solid was collected by filtration, washed, dried and then recrystallised from toluene-light petroleum to give the title compound, m.p. 127°-129° C.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. filtrationThe solid isonitroso-acetanilide intermediate was collected by filtration
  4. washwashed
  5. customdried
  6. temperatureThis material was cooled in an ice-salt bath
  7. additionconcentrated sulphuric acid (48 ml) was added dropwise
  8. additionAfter addition
  9. additionpoured
  10. customonto crushed ice
  11. filtrationThe resulting red solid was collected by filtration
  12. washwashed
  13. customdried
  14. customrecrystallised from toluene-light petroleum

出典と根拠

ORDレコード
ord-6fbb5b4d21a2410f94baa38992075c21
出典データセット
uspto-grants-1996_12
特許番号
US05585378

反応ノート

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