Dimethylformamide → 6-Amino-5-methylpyridine-3-carbonitrile

HRID 2113556Notes

Reaction equation

HRID 2113556 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH3:10][N:11](C=O)C>>[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:10]#[N:11])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 1379342-Amino-5-bromo-3-methylpyridine

Product 1

HCID 224828436-Amino-5-methylpyridine-3-carbonitrileYield 70%

Conditions

Temperature
150 °C

Procedure

A mixture of 2-Amino-5-bromo-3-methylpyridine (15.49 g, 82.8 mmol) and Cu(I)CN (9.27 g, 103.5 mmol) in DMF (160 mL) was heated at 150° C. for 24 h. The reaction mixture was poured onto water and the solid which formed was extracted by using ethylacetate (600 mL, 3 times) from aq. NH4OH. The solvent was evaporated and the precipitate purified by chromatography (SiO2, hexanes/EtOAc 4:6). Yield 70%, mp 198-200° C., (Lit. mp 203-205° C.; see Dunn A. D. and Norrie R. J. Prakt. Chem./Chem.-Ztg, 338 (7), 663-666 (1996). Lit. melting point not reported via palladium-catalyzed cyanation; see Maligres, P. et al., Tetrahedron Lett., 40, 8193-8195 (1999).

Workup

  1. additionThe reaction mixture was poured onto water
  2. customthe solid which formed
  3. extractionwas extracted
  4. customThe solvent was evaporated
  5. customthe precipitate purified by chromatography (SiO2, hexanes/EtOAc 4:6)

Sources & evidence

ORD record
ord-e7185b81e3a241a497c40cc49ada2d61
Source dataset
uspto-grants-2008_10
Patent number
US07432278B2

Reaction notes

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