Dimethylformamide → HCID 12274195, compound

HRID 1283126Notes

Reaction equation

HRID 1283126 reaction equation
[C-]#N.[K+].Cl[CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[O:18][C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[CH2:11][C:10]=2[CH:19]=1.[CH3:20][N:21](C)C=O>O>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]2[CH2:11][C:10]3[CH:19]=[C:6]([CH2:5][C:20]#[N:21])[CH:7]=[CH:8][C:9]=3[O:18][C:13]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 12274208HCID 12274208, compound

Product 1

HCID 12274195HCID 12274195, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 7.8 g of potassium cyanide in 20 ml of water is added dropwise to a mixture of 23 g of 7-chloromethyl-5H-[1]benzopyrano[2,3-b]-pyridine and 200 ml of dimethylformamide, and the whole mixture is allowed to stand at 55°-60°C for 2 hours. The reaction mixture is poured into a large amount of water, and the crystalline precipitate is filtered off, washed with water and recrystallized from aqueous dioxane to give 20 g of 5H-[1]-benzopyrano[2,3-b]pyridin-7-yl-acetonitrile melting at 166°-167°C.

Workup

  1. filtrationthe crystalline precipitate is filtered off
  2. washwashed with water
  3. customrecrystallized from aqueous dioxane

Sources & evidence

ORD record
ord-b56307b9f6a447f6ba371e23969ce443
Source dataset
uspto-grants-1976_08
Patent number
US03974168

Reaction notes

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