Hydrochloric Acid → 2-(6-bromo-1H-indol-3-yl)acetonitrile

HRID 2215747ノート

反応式

HRID 2215747 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11]N(C)C)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C-]#N.[Na+].[CH3:18][N:19](C=O)C.Cl>O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][C:18]#[N:19])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 133840941-(6-Bromo-1H-indol-3-yl)-N,N-dimethylmethanamine

生成物 1

HCID 158193282-(6-bromo-1H-indol-3-yl)acetonitrile収率 79%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

6-Bromo-N,N-dimethyl-1H-indole-3-methanamine (7.76 g, 30.6 mmol) and NaCN (1.95 g, 39.8 mmol, 1.30 eq.) were combined with DMF (40 mL) and water (40 mL). The mixture was heated to reflux for 6 hours, then cooled to rt. Aqueous 1N HCl (40 mL) was added, and the product was extracted with EtOAc. The organic layer was washed with water and dried (MgSO4). The solvent was removed in vacuo to give 5.70 g (79%) of the title compound, that was 79% pure by HPLC area, containing 14% 6-bromoindole. The material was used without purification in the subsequent step.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. extractionthe product was extracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-cc8d90fcc6be4ac29a20aa06ca04345e
出典データセット
uspto-grants-2006_09
特許番号
US07109229B2

反応ノート

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