Sodium Cyanide → HCID 21183731, compound

HRID 1384804Notes

Reaction equation

HRID 1384804 reaction equation
Br[CH2:2][C:3]1[C:15]2[C:14]3[CH:13]=[C:12]([F:16])[CH:11]=[CH:10][C:9]=3[N:8]([CH2:17][CH3:18])[C:7]=2[C:6](=[O:19])[N:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:4]=1.[C-:26]#[N:27].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[CH2:17]([N:8]1[C:9]2[CH:10]=[CH:11][C:12]([F:16])=[CH:13][C:14]=2[C:15]2[C:3]([CH2:2][C:26]#[N:27])=[N:4][N:5]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:6](=[O:19])[C:7]1=2)[CH3:18]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 21183748HCID 21183748, compound

Product 1

HCID 21183731HCID 21183731, compoundYield 93.3%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A two-phase mixture of 7.2 g (18 mmol) of 1-(bromomethyl)-5-ethyl-8-fluoro-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-4-one, of 3.53 g (72 mmol) of sodium cyanide and of 0.58 g (1.8 mmol) of tetrabutylammonium bromide in 300 ml of dichloromethane and 150 ml of water is stirred vigorously for 12 h. The organic phase is separated, washed several times with water, dried over magnesium sulphate and concentrated under reduced pressure. 5.8 g (16.8 mmol) of compound are isolated, which compound is used as is in the following stage.

Workup

  1. customThe organic phase is separated
  2. washwashed several times with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-831b0a07d37444f39df9f9f7e1e1034b
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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