Methyl iodide → HCID 15581183, compound

HRID 1283127Notes

Reaction equation

HRID 1283127 reaction equation
[Na].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[CH2:8][C:9]3[CH:15]=[C:14]([CH:16]([C:20]#[N:21])[C:17]([CH3:19])=[O:18])[CH:13]=[CH:12][C:10]=3[O:11][C:3]=12.[CH3:22]I>CN(C)C=O>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[CH2:8][C:9]3[CH:15]=[C:14]([C:16]([C:20]#[N:21])([CH3:22])[C:17](=[O:18])[CH3:19])[CH:13]=[CH:12][C:10]=3[O:11][C:3]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 13066472HCID 13066472, compound

Product 1

HCID 15581183HCID 15581183, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.9 g of sodium salt of 1-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)-1-cyano-acetone is dissolved in 15 ml of dried dimethylformamide, 1.6 g of methyl iodide is added to the solution with stirring, and the mixture is stirred at room temperature for 1.5 hours. The reaction mixture is concentrated, and water is added to the oily residue. The crystalline precipitate is filtered off and recrystallized from ethanol to give 2.2 g of 3-(5H-[1]-benzopyrano[2,3-b]pyridin-7-yl)-3-cyano-2-butanone as white needles melting at 163.5°-164.5°C.

Workup

  1. stirringthe mixture is stirred at room temperature for 1.5 hours
  2. concentrationThe reaction mixture is concentrated
  3. additionwater is added to the oily residue
  4. filtrationThe crystalline precipitate is filtered off
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1ab0cf009b7044e1a84d958dd91798ba
Source dataset
uspto-grants-1976_08
Patent number
US03974168

Reaction notes

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