Potassium Cyanide → HCID 14520028, compound

HRID 2072904Notes

Reaction equation

HRID 2072904 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][N:5]([C:7]([C:9]1[C:18]2[C:13](=[C:14](Br)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[O:22][CH3:23])=[O:8])[CH3:6].CN1CCCC1=O.[F:32][C:33]([F:38])([F:37])C([O-])=O.[Na+].[C-]#N.[K+]>O.C(OCC)(=O)C.[Cu]I.C(OCC)C>[CH3:1][O:2][C:3](=[O:24])[CH2:4][N:5]([C:7]([C:9]1[C:18]2[C:13](=[C:14]([C:33]([F:38])([F:37])[F:32])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[O:22][CH3:23])=[O:8])[CH3:6]

Participants

9

Reactant 4

HCID 9032Potassium CyanideHCID 13387N-methyl-2-pyrrolidoneHCID 517019Sodium TrifluoroacetateHCID 14520027HCID 14520027, compound

Product 1

HCID 14520028HCID 14520028, compoundYield 89%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of N-[5-bromo-2,6-dimethoxy-1-naphthalenyl)carbonyl]-N-methylglycine methyl ester (6.24 g, 15.7 mmol, described in Example 3), copper (I) iodide (11.99 g, 62.9 mmol), 1-methyl-2-pyrrolidinone (300 mL), and sodium trifluoroacetate (17.08 g, 12.6 mmol) was heated at 180° C. for 2 hours under an argon atmosphere. Upon cooling the residue was suspended in water (1 L) and ethyl ether (2 L) and potassium cyanide (30 g) were added with stirring. The organic layer was separated and washed sequentially with saturated NaHCO3, water (3X), saturated NaCl and then dried over Na2SO4. After concentration, silica gel chromatography using 10:1 CH2Cl2 :ethyl acetate as eluent gave 4.32 g (71% yield) of the title compound as a pale brown oil.

Workup

  1. temperatureUpon cooling the residue
  2. customThe organic layer was separated
  3. washwashed sequentially with saturated NaHCO3, water (3X), saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration, silica gel chromatography

Sources & evidence

ORD record
ord-37645a22c3884539ab1ecc8ec8737cb8
Source dataset
uspto-grants-1990_04
Patent number
US04914243

Reaction notes

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