Dimethylamine → 2-(Dimethylamino)pyridine-4-carbonitrile

HRID 1155544Notes

Reaction equation

HRID 1155544 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].O1CCCC1.[CH3:15][NH:16][CH3:17]>C1(C)C=CC=CC=1>[CH3:15][N:16]([CH3:17])[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 131452572-(Dimethylamino)pyridine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 10 g. (72 mmoles) of 2-chloroisonicotinonitrile, 30 ml. of tetrahydrofuran, 100 ml. of toluene and 20 ml. (0.3 mole) of dimethylamine was placed in a steel bomb and heated at 190° C. for 4 hours. The bomb was cooled and the mixture removed and filtered. The residue, remaining after the filtrate was concentrated, was dissolved in water, which was subsequently extracted with ether (3×40 ml.). The combined extracts were dried and concentrated to the crude product. Recrystallization from petroleum ether gave 7.4 g. (69%) of the pure product, m.p. 63°-66° C.

Workup

  1. additionA mixture of 10 g
  2. temperatureThe bomb was cooled
  3. customthe mixture removed
  4. filtrationfiltered
  5. concentrationwas concentrated
  6. dissolutionwas dissolved in water
  7. extractionwhich was subsequently extracted with ether (3×40 ml.)
  8. customThe combined extracts were dried
  9. concentrationconcentrated to the crude product
  10. customRecrystallization from petroleum ether
  11. customgave 7.4 g

Sources & evidence

ORD record
ord-db1a4ed874d047f8955288153d08d50e
Source dataset
uspto-grants-1981_11
Patent number
US04302464

Reaction notes

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