Sodium Acetate → Methyl 3-methylflavone-8-carboxylate

HRID 979990Notes

Reaction equation

HRID 979990 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:11]=1)[O:8][C:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:6]([CH3:22])[C:5]2=[O:23].C([O-])(=O)C.[Na+].[H][H]>[C].[Pd].C(O)(C)C>[CH3:22][C:6]1[C:5](=[O:23])[C:4]2[C:9](=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:11]=[CH:2][CH:3]=2)[O:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 13335993Methyl 6-chloro-3-methylflavone-8-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 7582698Methyl 3-methylflavone-8-carboxylateYield 82.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

Into a pressure reactor were placed 1.5 g (4.57 m mole) of methyl 6-chloro-3-methylflavone-8-carboxylate, 1.8 g (14.2 m mole) of sodium acetate, 150 ml of isopropanol and 0.075 g of 5% palladium-carbon. After the atmosphere was replaced with hydrogen gas, reaction was conducted at 70° C. under a pressure of 5.0 kg/cm2G for 6 hours. Thereafter the contents were withdrawn from the reactor and were subjected to filtration while being hot to remove the catalyst. The solvent was recovered from the filtrate to provide 1.1 g (82.1%) of white needle-like crystals which melt at 162.2° to 164.8° C. The crystals were recrystallized from alcohol to obtain a product having a melting point of 166.4° to 168.2° C. The product was found identical in melting point with the compound prepared by the conventional method. When the product of this example and the compound prepared by the conventional method were melted together, the melting point was not lower than that of the product of this example.

Workup

  1. customInto a pressure reactor were placed
  2. customThereafter the contents were withdrawn from the reactor
  3. filtrationwere subjected to filtration
  4. customto remove the catalyst
  5. customThe solvent was recovered from the filtrate

Sources & evidence

ORD record
ord-bb2f96e25bbf4017b8537ff6abab3e19
Source dataset
uspto-grants-1987_01
Patent number
US04634768

Reaction notes

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