Water → HCID 13066474, compound

HRID 1283122Notes

Reaction equation

HRID 1283122 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH2:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12.O.[CH3:20]I>[Na].C(O)(C)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH:15]([CH3:20])[C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12

Participants

6

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 13066473HCID 13066473, compound

Product 1

HCID 13066474HCID 13066474, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 5360545SodiumSolvent

Procedure

24 g of 5H-[1]benzopyrano[ 2,3-b]pyridin-7-yl-acetone is dissolved in a solution of 2.5 g of metallic sodium in 120 ml of isopropyl alcohol at 50°-60°C with stirring. The solution is cooled to 40°C with water, 17.2 g of methyl iodide is added, and the mixture is stirred under reflux for 1 hour. The isopropyl alcohol is distilled off under reduced pressure, and the residue is dissolved in chloroform. After water cooling, the solution is dried over anhydrous magnesium sulfate and concentrated, and the residue is recrystallized from isopropyl alcohol to give 19 g of 3-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)-2-butanone melting at 136°-136°C.

Workup

  1. additionis added
  2. stirringthe mixture is stirred
  3. temperatureunder reflux for 1 hour
  4. distillationThe isopropyl alcohol is distilled off under reduced pressure
  5. dissolutionthe residue is dissolved in chloroform
  6. dry with materialAfter water cooling, the solution is dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customthe residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-7d0040f88a0246138f33a8b646bda9f9
Source dataset
uspto-grants-1976_08
Patent number
US03974168

Reaction notes

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