Water → HCID 13362115, compound

HRID 1633142Notes

Reaction equation

HRID 1633142 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25].O>CN(C=O)C>[C:24]([CH2:23][CH2:22][CH2:21][CH2:20][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:1])=[C:3]1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)#[N:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 794355-BromopentanenitrileHCID 155913683-Methyl-2-(3-pyridyl)indole

Product 1

HCID 13362115HCID 13362115, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3-methyl-2-(3-pyridyl)indole (2.09 g) in 12 ml of DMF is added to a suspension of 0.528 g of 50% sodium hydride (dispersion in mineral oil) in 6 ml of DMF at 0°. The mixture is stirred at 0° for 0.5 hour and is treated with a solution of 1.78 g of 5-bromovaleronitrile in 4 ml of DMF. This mixture is stirred at room temperature overnight and is poured into 125 ml of water. This is extracted with 2×50 ml of ether, the extract is washed with 3×20 ml of water and dried over MgSO4 to give 1-(4-cyanobutyl)-3-methyl-2-(3-pyridyl)-indole as an oil.

Workup

  1. stirringThis mixture is stirred at room temperature overnight
  2. extractionThis is extracted with 2×50 ml of ether
  3. washthe extract is washed with 3×20 ml of water
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-a83a1aded6144b77a4f66a0151c3a1f4
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

Loading…