Hydrochloric Acid → N-acetyl-5-bromo-7-cyanoindoline

HRID 4928

反応式

HRID 4928 の反応式
Cl.[C:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([Br:15])=[CH:11][C:12]=2N)[CH2:7][CH2:6]1)(=[O:4])[CH3:3].N([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[C-:26]#[N:27].[Na+]>[Cu](C#N)C#N>[C:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([Br:15])=[CH:11][C:12]=2[C:26]#[N:27])[CH2:7][CH2:6]1)(=[O:4])[CH3:3]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 10340Sodium CarbonateHCID 197113381-(7-Amino-5-bromoindolin-1-yl)ethanoneHCID 23668193Sodium Nitrite

生成物 1

HCID 19797208N-acetyl-5-bromo-7-cyanoindoline収率 81.1%

試薬・触媒・溶媒 1

HCID 178418260HCID 178418260、化合物溶媒

反応条件

温度
-1 °C

実験手順

Into 6N hydrochloric acid (178.5 ml) was suspended N-acetyl-7-amino-5-bromoindoline (51.0 g), and aqueous solution (212 ml) of sodium nitrite (21.2 g) was dropwise added thereto under cooling with stirring over 30 minutes and at the inside temperature of not higher than -1° C. After stirred for 30 minutes at the temperature as such, sodium carbonate was added to the reaction mixture to neutralize it. This reaction mixture was poured into aqueous solution (200 ml) of copper cyanide (27.5 g) and sodium cyanide (30.7 g), and the mixture was allowed to stand for one night at room temperature. The reaction mixture was again subjected to stirring for 30 minutes at the inside temperature of 50° C. and was cooled to give a deposited crystal, which was then collected by filtration, washed with water and dried. The crude crystal was recrystallized from acetonitrile to give the intended compound 43.0 g (81.1%). M.P.: 170°-175° C.

後処理

  1. additionwas dropwise added
  2. temperatureunder cooling
  3. additionwas added to the reaction mixture
  4. waitto stand for one night at room temperature
  5. stirringto stirring for 30 minutes at the inside temperature of 50° C.
  6. temperaturewas cooled
  7. customto give a deposited crystal, which
  8. filtrationwas then collected by filtration
  9. washwashed with water
  10. customdried
  11. customThe crude crystal was recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-45f32967a0dc4124843cfe2d5c8768c7
出典データセット
uspto-grants-1993_09
特許番号
US05242912

関連ノート

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