Acetic Acid → Y 9000

HRID 1579390Notes

Reaction equation

HRID 1579390 reaction equation
C(O)(=O)C.S(=O)(=O)(O)O.[O:10]=[C:11]1[C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[O:14][C:13]2[CH:21]=[CH:22][C:23]([C:25]([CH:27](C(OCC)=O)C(OCC)=O)=[O:26])=[CH:24][C:12]1=2>O>[C:25]([C:23]1[CH:22]=[CH:21][C:13]2[O:14][C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:20]3[C:11](=[O:10])[C:12]=2[CH:24]=1)(=[O:26])[CH3:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 21568404HCID 21568404, compound

Product 1

HCID 198324Y 9000

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 7.5 ml of glacial acetic acid, 0.9 ml of concentrated sulfuric acid, 4.5 ml of water and 4.6 g of diethyl 2-(5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-7-yl-carbonyl)malonate is stirred under reflux for 2 hours. The reaction mixture is poured into 50 ml of cool water. The crystalline precipitate is filtered off, and suspended in water. The suspension is alkalified with 10% sodium hydroxide under ice cooling, and extracted with chloroform. The extract is washed thoroughly with water, dried, and concentrated. The residue is recrystallized from toluene to give 7 -acetyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine melting at 194°-195°C.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationThe crystalline precipitate is filtered off
  3. extractionextracted with chloroform
  4. washThe extract is washed thoroughly with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-adba64faaa814d8fb4314aba66ca6464
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

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