4-Cyanopyridine → HCID 23499332, compound

HRID 260709Notes

Reaction equation

HRID 260709 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#N.Br[C:10]1[CH:11]=[C:12]([O:16][CH3:17])[CH:13]=[CH:14][CH:15]=1.[Mg].[O:19]1CCCC1>>[CH3:17][O:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)=[O:19]

Participants

5

Reactant 4

HCID 75064-CyanopyridineHCID 8028Tetrahydrofuran2×HCID 169713-BromoanisoleHCID 5462224Magnesium

Product 1

HCID 23499332HCID 23499332, compoundYield 63%

Conditions

Temperature
25 °C

Procedure

A solution of 4-cyanopyridine (20.8 g, 200 mmol) in tetrahydrofuran (THF) was added to the Grignard reagent prepared from 3-bromoanisole (37.4 g, 200 mmol) and magnesium (4.8 g, 200 mmol) in THF (400 ml) at -78° C. The solution was allowed to warm to 25° C. and quenched with ammonium chloride solution. The organic layer was separated and washed with water and 3N hydrochloric acid. The acid washes were stirred for 0.5 hr and neutralized with 50% sodium hydroxide. The basic mixture was extracted with ether. The extracts were dried and concentrated in vacuo. The crude material was crystallized from hexane to give 4-(3-methoxybenzoyl)pyridine (27 g, 63%).

Workup

  1. customquenched with ammonium chloride solution
  2. customThe organic layer was separated
  3. washwashed with water and 3N hydrochloric acid
  4. extractionThe basic mixture was extracted with ether
  5. customThe extracts were dried
  6. concentrationconcentrated in vacuo
  7. customThe crude material was crystallized from hexane

Sources & evidence

ORD record
ord-197a7fb711d44f4c80ed8728c3b1a6d5
Source dataset
uspto-grants-1996_06
Patent number
US05530012

Reaction notes

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