Sulfuric Acid → HCID 13066473, compound

HRID 1283128Notes

Reaction equation

HRID 1283128 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH:15](C#N)[C:16]([CH3:18])=[O:17])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12.N1C=CC=C2CC3C=C(CC#N)C=CC=3OC=12.S(=O)(=O)(O)O.[OH-].[Na+]>O.C(OCC)(=O)C>[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:17])[CH3:18])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 12274195HCID 12274195, compoundHCID 13066472HCID 13066472, compound

Product 1

HCID 13066473HCID 13066473, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)-1-cyano-acetone prepared from 33 g of 5H-[1]benzopyrano[2,3-b]pyridin-7-yl-acetonitrile and 75 ml of ethyl acetate is added in small portions to 75 ml of concentrated sulfuric acid with stirring, while the temperature is maintained at below 20°C by cooling with ice. 225 ml of water is added at a stretch to the mixture, and the whole mixture is stirred under reflux for 5 hours. The reaction mixture is ice-cooled and strongly alkalified by adding 30% sodium hydroxide with stirring. The crystalline precipitate is extracted with chloroform, and the extract is washed with water and dried over anhydrous sodium sulfate. The chloroform is distilled off, and the residue is recrystallized from isopropyl alcohol to give 25 g of 5H-[1]benzopyrano[2,3-b]pyridin-7-yl-acetone as white needles melting at 124°-125°C.

Workup

  1. temperatureis maintained at below 20°C
  2. temperatureby cooling with ice
  3. stirringthe whole mixture is stirred
  4. temperatureunder reflux for 5 hours
  5. temperaturecooled
  6. stirringwith stirring
  7. extractionThe crystalline precipitate is extracted with chloroform
  8. washthe extract is washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe chloroform is distilled off
  11. customthe residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-38408bded57c400487377470f9539947
Source dataset
uspto-grants-1976_08
Patent number
US03974168

Reaction notes

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