3-Cyano-2,6-dichloro-4-methylpyridine → (E)-2,6-Dichloro-4-(2-(dimethylamino)vinyl)nicotinonitrile

HRID 1034943Notes

Reaction equation

HRID 1034943 reaction equation
[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>C(O)(C)C>[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[CH:7]=[C:6](/[CH:11]=[CH:14]/[N:15]([CH3:17])[CH3:16])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 701313-Cyano-2,6-dichloro-4-methylpyridineHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 58093913(E)-2,6-Dichloro-4-(2-(dimethylamino)vinyl)nicotinonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

To 2,6-dichloro-4-methylnicotinonitrile (20.3 g, 0.108 mol) in 200 mL of isopropyl alcohol is added N,N-dimethylformamide dimethylacetal (14.4 mL, 0.108 mol) and the reaction is stirred at 65° C. for 18 hrs. After the reaction is cooled to ambient temperature, the precipitate is collected by filtration, washed with 50 mL of isopropyl alcohol, and air dried giving (E)-2,6-Dichloro-4-(2-(dimethylamino)vinyl)nicotinonitrile as a yellow solid. MS (ES+) calcd. 242.02. found 242.10 (MH+). H-NMR (600 MHz, DMSO-d6) 2.90 (br.s, 3H), 3.17 (br.s, 3H), 5.05 (d, J=12.6 Hz, 1H), 7.61 (s, 1H), 8.09 (d, J=12.6 Hz, 1H).

Workup

  1. temperatureAfter the reaction is cooled to ambient temperature
  2. filtrationthe precipitate is collected by filtration
  3. washwashed with 50 mL of isopropyl alcohol, and air
  4. customdried

Sources & evidence

ORD record
ord-6a049bcd94eb4f10a1237941cfb83371
Source dataset
uspto-grants-2013_10
Patent number
US08546370B2

Reaction notes

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