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

HRID 2215747Notes

Reaction equation

HRID 2215747 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cc8d90fcc6be4ac29a20aa06ca04345e
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

Loading…