3-Cyanopyridine → HCID 69942718, compound

HRID 428315Notes

Reaction equation

HRID 428315 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Mg].[C:11]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)#N.Cl.[OH2:20]>C(OCC)C.CC(O)C>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:14]1[C:13]([C:11]([C:13]2[C:14]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[O:8][CH3:9])=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:20])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

8

Reactant 5

HCID 793-CyanopyridineHCID 313Hydrochloric AcidHCID 962WaterHCID 113582-BromoanisoleHCID 5462224Magnesium

Product 1

HCID 69942718HCID 69942718, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 3776IsopropanolSolvent

Procedure

A solution of 2-bromoanisole (21 g, 0.11 mol) in diethyl ether (100 mL) was added to magnesium turnings during 45 minutes with heating. After the addition the reflux was continued for 15 min. The Grignard reagent was cooled to 0° C. and a solution of 3-cyanopyridine (10 g, 0.10 mol) in diethyl ether (100 mL) was added dropwise. The mixture was refluxed for a few minutes. Hydrochloric acid (20 mL, 0.24 mol, conc.) and 2-propanol (20 mL) were added and the reflux was continued for 30 min. Water and diethyl ether were added and the phases separated. The water-phase was made alkaline (2M NaOH) and was extracted with diethyl ether. The combined organic phases were dried (MgSO4) and evaporated to yield 17 g. The crude was chromatographed on silica (toluene-ethyl acetate 19:1) to give 3.75 g (19%). 1H NMR (CDCl3-d) δ3.76 (s, 3H), 7.01 (d, 1H), 7.10 (t, 1H), 7.41 (dd, 1H), 7.46 (dd, 1H), 4.53 (m, 1H), 8.12 (d, 1H), 8.75 (s, 1H) and 8.94 (s,

Workup

  1. temperaturewith heating
  2. additionAfter the addition the reflux
  3. temperatureThe mixture was refluxed for a few minutes
  4. waitthe reflux was continued for 30 min
  5. customthe phases separated
  6. extractionwas extracted with diethyl ether
  7. dry with materialThe combined organic phases were dried (MgSO4)
  8. customevaporated
  9. customto yield 17 g
  10. customThe crude was chromatographed on silica (toluene-ethyl acetate 19:1)
  11. customto give 3.75 g (19%)

Sources & evidence

ORD record
ord-79751d69334d4a37901c9c8d400b380c
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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