Sodium Cyanide → HCID 87538453, compound

HRID 1443276Notes

Reaction equation

HRID 1443276 reaction equation
Cl[C:2]1[C:3]([OH:31])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([NH:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=1[CH:15]=[CH:16][NH:17][C:18]3=[O:23])[C:7]([OH:28])([C:24]([F:27])([F:26])[F:25])[CH2:6][C:5]2([CH3:30])[CH3:29].[C-:32]#[N:33].[Na+]>CN1CCCC1=O.[Ni](Br)Br>[OH:31][C:3]1[C:4]2[C:5]([CH3:30])([CH3:29])[CH2:6][C:7]([OH:28])([C:24]([F:25])([F:27])[F:26])[CH:8]([NH:12][C:13]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:14]=3[CH:15]=[CH:16][NH:17][C:18]4=[O:23])[C:9]=2[CH:10]=[CH:11][C:2]=1[C:32]#[N:33]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 87539079HCID 87539079, compound

Product 1

HCID 87538453HCID 87538453, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 278492Nickel(II) bromideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

75 mg (0.166 mmol) of 5-(6-chloro-2,5-dihydroxy-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-ylamino)-2H-isoquinolin-1-one is dissolved in 1.3 ml of 1-methyl-2-pyrrolidinone and reacted in the microwave with 16.27 mg (0.332 mmol) of sodium cyanide and 36.27 mg (0.166 mmol) of nickel(II) bromide, as described in Example 160. The black reaction mixture is added via a glass fiber filter. After washing with ethyl acetate, the filtrate is also mixed with an additional 60 ml of ethyl acetate. It is shaken with water and with brine. After drying, the solvent is spun off, and the residue is chromatographed on silica gel (amine plate; mobile solvent: methanol/dichloromethane). 16.2 mg (22.1%) of the desired nitrile is isolated.

Workup

  1. customThe black reaction mixture
  2. additionis added via a glass fiber
  3. filtrationfilter
  4. washAfter washing with ethyl acetate
  5. additionthe filtrate is also mixed with an additional 60 ml of ethyl acetate
  6. customAfter drying
  7. customthe residue is chromatographed on silica gel (amine plate; mobile solvent: methanol/dichloromethane)

Sources & evidence

ORD record
ord-774ad3ad991e44698530c7ee054ff7a0
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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