Sulfuric Acid → HCID 21568404, compound

HRID 1579385Notes

Reaction equation

HRID 1579385 reaction equation
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[O:13]=[C:14]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[O:17][C:16]2[CH:24]=[CH:25][C:26]([C:28](Cl)=[O:29])=[CH:27][C:15]1=2.S(=O)(=O)(O)O>O.C(O)C.ClC1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[O:13]=[C:14]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[O:17][C:16]2[CH:24]=[CH:25][C:26]([C:28]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:29])=[CH:27][C:15]1=2

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 5462224MagnesiumHCID 53808777HCID 53808777, compound

Product 1

HCID 21568404HCID 21568404, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 5943Carbon TetrachlorideSolventHCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
65 °C

Procedure

0.57 g of magnesium, 0.8 ml of carbon tetrachloride and 3.6 ml of absolute ethanol are placed in a four-necked flask fitted with a dropping funnel, a thermometer, a reflux condenser and a stirrer. 36.5 ml of chlorobenzene is added, and then a mixture of 2.67 g of diethyl malonate, 18 ml of chlorobenzene and 12.6 ml of absolute ethanol is added dropwise, while the temperature is maintained at 65°C. The mixture is allowed to stand at 85°C for 1 hour to complete the reaction. After cooling with water, 4 g of 5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-7-carboxylic acid chloride is added, and the mixture is stirred at 30°-35°C for 1.5 hours. To the reaction mixture is added a mixture of 1 ml of concentrated sulfuric acid and 7 ml of water is added dropwise with stirring under ice cooling, and the precipitate (sodium sulfate) is removed by filtration. The residue is washed with water, dried, and concentrated. The residue is recrystallized from ethanol to give diethyl 2-(5-oxo-5H-[1]benzopyrano[2,3-b]pyridine- 7-yl-carbonyl)malonate as white crystals melting at 137°-138.5°C.

Workup

  1. customfitted with a dropping funnel
  2. additionis added dropwise, while the temperature
  3. customthe reaction
  4. additionis added
  5. additionTo the reaction mixture is added
  6. additionis added dropwise
  7. stirringwith stirring under ice cooling
  8. customthe precipitate (sodium sulfate) is removed by filtration
  9. washThe residue is washed with water
  10. customdried
  11. concentrationconcentrated
  12. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-f9d4cf9aa4bb400c86db9758784f499e
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

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