Malonic Acid → HCID 20517749, compound

HRID 28239Notes

Reaction equation

HRID 28239 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].O[C:6]1[CH:19]=[C:18]2[C:9]([CH:10]=[CH:11][C:12]3[O:13][CH:14]=[C:15](C=O)[C:16](=[O:20])[C:17]=32)=[CH:8][CH:7]=1.[C:23](O)(=O)[CH2:24][C:25]([OH:27])=[O:26]>N1C=CC=CC=1>[C:1]([O:4][C:6]1[CH:19]=[C:18]2[C:9]([CH:10]=[CH:11][C:12]3[O:13][CH:14]=[C:15]([C:24](=[CH2:23])[C:25]([OH:27])=[O:26])[C:16](=[O:20])[C:17]=32)=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 867Malonic Acid2×HCID 867372399-hydroxy-1-oxo-1H-naphtho[2,1-b]pyran-2-carboxaldehyde acetate

Product 1

HCID 20517749HCID 20517749, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 9-hydroxy-1-oxo-1H-naphtho[2,1-b]pyran-2-carboxaldehyde acetate (10.0 g, 0.0354 m) and malonic acid (4.0 g, 0.0354 m) in pyridine (100 ml) is refluxed for 45 minutes. Additional malonic acid (1.0 g, 0.00885 m, 0.25 eq.) is added and the reaction refluxed for 30 minutes. The solvent is removed under reduced pressure to give a sludge from which product crystallizes on the addition of acetone. After filtering the product, recrystallization from DMF gives cocoa crystals (2.75 g, 24%), m.p. dec>290° C.

Workup

  1. temperatureis refluxed for 45 minutes
  2. temperaturethe reaction refluxed for 30 minutes
  3. customThe solvent is removed under reduced pressure
  4. customto give a sludge from which product
  5. customcrystallizes on the addition of acetone
  6. filtrationAfter filtering
  7. customthe product, recrystallization from DMF

Sources & evidence

ORD record
ord-46b3050d1fbb499aa5a8ba747aa797f6
Source dataset
uspto-grants-1980_09
Patent number
US04225722

Reaction notes

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