Tributylamine → 2-Methyl-5-nitrocinnamonitrile

HRID 1156464Notes

Reaction equation

HRID 1156464 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](Cl)=O.[C:14](#[N:17])[CH:15]=C.C(N(CCCC)CCCC)CCC>CC1C=CC(C)=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[CH:4]=[CH:15][C:14]#[N:17]

Participants

6

Reactant 3

HCID 7622TributylamineHCID 7855AcrylonitrileHCID 44365682-Methyl-5-nitrobenzoyl chloride

Product 1

HCID 541228552-Methyl-5-nitrocinnamonitrile

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

0.336 g (1.5 millimols) of palladium acetate, 29.93 g (150 millimols) of 2-methyl-5-nitrobenzoyl chloride, 9.94 g (187.5 millimols) of acrylonitrile and 27.80 g (150 millimols) of tri-n-butylamine, in 150 ml of p-xylene, are stirred for 80 minutes at 130°. The mixture is then extracted, and dried, as described in Example 68. The crude product is chromatographed on silica gel in toluene and is then recrystallised from carbon tetrachloride/cyclohexane. 6.3 g (22% of theory) of white crystals, of melting point 115.6° C., are obtained. Analysis for C10H8N2O2 : calculated C 63.83%, H 4.29%, N 14.89%; found C 63.8%, H 4.2%, N 15.1%.

Workup

  1. extractionThe mixture is then extracted
  2. customdried
  3. customThe crude product is chromatographed on silica gel in toluene
  4. customis then recrystallised from carbon tetrachloride/cyclohexane
  5. custom6.3 g (22% of theory) of white crystals, of melting point 115.6° C., are obtained

Sources & evidence

ORD record
ord-38825f6c6ada47bc9d9b20d238d375d5
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

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