Dimethylformamide → HCID 12274184, compound

HRID 1579444Notes

Reaction equation

HRID 1579444 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:15][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[O:16])[C:7]=2[CH:17]=1.[CH3:18][N:19](C)C=O.[C-]#N.[Na+]>O>[C:18]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:15][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[O:16])[C:7]=2[CH:17]=1)#[N:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 122742035H-[1]Benzopyrano[2,3-b]pyridin-5-one, 7-(bromomethyl)-

Product 1

HCID 12274184HCID 12274184, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 25 g of 7-bromomethyl-5-oxo-5H-[1]benzopyrano-[2,3-b]pyridine and 175 ml of dimethylformamide is added 5.1 g of sodium cyanide under ice cooling. The mixture is stirred at room temperature for 2 hours, and then 300 ml of water is added to the reaction mixture. The resulting crystalline precipitate is filtered off, washed with water, and recrystallized from dioxane to give 17 g of 7-cyanomethyl-5-oxo-5H-[1]-benzopyrano[2,3-b]pyridine melting at 198°-201°C.

Workup

  1. filtrationThe resulting crystalline precipitate is filtered off
  2. washwashed with water
  3. customrecrystallized from dioxane

Sources & evidence

ORD record
ord-1b8759658c91464dba238e2d0c3b8381
Source dataset
uspto-grants-1976_01
Patent number
US03931205

Reaction notes

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