Water → HCID 68581052, compound

HRID 2235984Notes

Reaction equation

HRID 2235984 reaction equation
Br[C:2]1[C:11]2[C:6]3=[C:7]([C:12](=[O:28])[N:13]([C:16]4[C:21]([CH:22]([CH3:24])[CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=4[CH:25]([CH3:27])[CH3:26])[C:14](=[O:15])[C:5]3=[CH:4][CH:3]=1)[CH:8]=[CH:9][CH:10]=2.[Cu][C:30]#[N:31].O>CN1CCCC1=O>[C:30]([C:2]1[C:11]2[C:6]3=[C:7]([C:12](=[O:28])[N:13]([C:16]4[C:17]([CH:25]([CH3:27])[CH3:26])=[CH:18][CH:19]=[CH:20][C:21]=4[CH:22]([CH3:24])[CH3:23])[C:14](=[O:15])[C:5]3=[CH:4][CH:3]=1)[CH:8]=[CH:9][CH:10]=2)#[N:31]

Participants

5

Reactant 3

HCID 962WaterHCID 10982967HCID 10982967, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 68581052HCID 68581052, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

24.8 g of 4-bromo-N-(2,6-diisopropylphenyl)naphthalene-1,8-dicarboximide and 7.5 g of copper(I) cyanide in 150 ml of N-methylpyrrolidone were heated at 210° C. for 4 hours. After cooling, water was added to the reaction mixture, producing a precipitate. The precipitate was filtered off, washed and dried. Column chromatography of the precipitate on silica gel (eluent: dichloromethane) gave 15.6 g of 4-cyano-N-(2,6-diisopropylphenyl)naphthalene-1,8-dicarboximide having a melting point of 291° C.

Workup

  1. temperatureAfter cooling
  2. customproducing a precipitate
  3. filtrationThe precipitate was filtered off
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-aede9b3802b046548afc3197eed0343f
Source dataset
uspto-grants-2010_05
Patent number
US07714044B2

Reaction notes

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