Toluene → HCID 54212925, compound

HRID 619118Notes

Reaction equation

HRID 619118 reaction equation
C[Si]([C:5]#[N:6])(C)C.I[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]2[CH2:20][C:21]([O:23][CH3:24])=[O:22].CNC1C=CC(I)=CC=1.C1(C)C=CC=CC=1>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]2[CH2:20][C:21]([O:23][CH3:24])=[O:22])#[N:6]

Participants

8

Reactant 4

HCID 1140TolueneHCID 82115Trimethylsilyl cyanideHCID 6454006Benzenamine, 4-iodo-N-methyl-HCID 54160516HCID 54160516, compound

Product 1

HCID 54212925HCID 54212925, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

1.1 ml of trimethylsilyl cyanide (8.4 mmol) followed by 0.15 g (0.13 mmol) of tetrakistriphenylphosphinepalladium are added to a solution of 0.50 g (1.4 mmol) of methyl 6-iodo-1-methyl-2-oxo-1,2-dihydro-4-quinolineacetate (prepared from N-methyl-4-iodoaniline according to the method described in Example 1) in 6 ml of anhydrous triethylamine. The reaction medium is then heated to reflux for 4 hours under a nitrogen atmosphere. After cooling to room temperature, the medium is poured into 60 ml of toluene and 60 ml of water. The organic phase is washed with water and the initial aqueous phase is re-extracted with dichloromethane. The organic phases are combined, dried over sodium sulphate and concentrated under vacuum. The residue is purified by flash chromatography on silica, eluting with a methanol/dichloromethane (5:95) mixture.

Workup

  1. temperatureThe reaction medium is then heated
  2. temperatureto reflux for 4 hours under a nitrogen atmosphere
  3. washThe organic phase is washed with water
  4. extractionthe initial aqueous phase is re-extracted with dichloromethane
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by flash chromatography on silica
  8. washeluting with a methanol/dichloromethane (5:95) mixture

Sources & evidence

ORD record
ord-f7d3515961e94f28b1cf521790e78106
Source dataset
uspto-grants-1999_09
Patent number
US05958924

Reaction notes

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