Methyl iodide → Ethyl 2-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)-2-cyanopropanoate

HRID 1579446Notes

Reaction equation

HRID 1579446 reaction equation
[Na].[C:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[O:17][C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH2:10][C:9]=2[CH:18]=1)#[N:3].[C:19](=O)([O:23]CC)[O:20][CH2:21][CH3:22].[CH3:27]I>C(O)C>[C:2]([C:4]([C:5]1[CH:6]=[CH:7][C:8]2[O:17][C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH2:10][C:9]=2[CH:18]=1)([CH3:27])[C:19]([O:20][CH2:21][CH3:22])=[O:23])#[N:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7766Diethyl CarbonateHCID 5360545SodiumHCID 12274195HCID 12274195, compound

Product 1

HCID 21568495Ethyl 2-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)-2-cyanopropanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.76 g of metallic sodium in 15 ml of ethanol is added to a mixture of 6.6 g of 7-cyanomethyl-5H-[1]benzopyrano[2,3-b]pyridine and 46 ml of diethyl carbonate, and the whole mixture is refluxed for 1 hour. After cooling, 5.2 g of methyl iodide is added to the reaction mixture. The temperature of the mixture is raised gradually, and the mixture is refluxed for 2 hours. The excess diethyl carbonate is distilled off, and toluene is added to the residue. The mixture is washed with water, and the toluene layer is dried. The toluene is distilled off, and the residue is recrystallized from isopropyl alcohol to give ethyl 2-cyano-2-(5H-[1]benzopyrano-[2,3-b]pyridin-7-yl)propionate melting at 119°-120°C.

Workup

  1. temperaturethe whole mixture is refluxed for 1 hour
  2. temperatureAfter cooling
  3. temperatureThe temperature of the mixture is raised gradually
  4. temperaturethe mixture is refluxed for 2 hours
  5. distillationThe excess diethyl carbonate is distilled off
  6. additiontoluene is added to the residue
  7. washThe mixture is washed with water
  8. dry with materialthe toluene layer is dried
  9. distillationThe toluene is distilled off
  10. customthe residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-aaf08c8efa8c415a8d5640f0bbe123f7
Source dataset
uspto-grants-1976_01
Patent number
US03931205

Reaction notes

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