Sodium Cyanide → HCID 21183754, compound

HRID 1384830Notes

Reaction equation

HRID 1384830 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][O:18][CH3:19])[C:7]=2[C:6](=[O:20])[N:5]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:4]=1.[C-:27]#[N:28].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[F:16][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:17][O:18][CH3:19])[C:7]3[C:6](=[O:20])[N:5]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:4]=[C:3]([CH2:2][C:27]#[N:28])[C:15]=3[C:14]=2[CH:13]=1

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 21183758HCID 21183758, compound

Product 1

HCID 21183754HCID 21183754, compoundYield 86.6%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A two-phase mixture of 2.8 g (6.7 mmol) of 1-(bromomethyl)-8-fluoro-5-(methoxymethyl)-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-4-one, of 1.3 g (26 mmol) of sodium cyanide and of 0.23 g (0.7 mmol) of tetrabutylammonium bromide in 100 ml of dichloromethane and 100 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. Diethyl ether is added and the precipitate is collected by filtration and dried under reduced pressure. 2.1 g (5.8 mmol) of solid are isolated, which solid 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
  5. additionDiethyl ether is added
  6. filtrationthe precipitate is collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-5dafebc7a1a84689b7086518f6c50bad
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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