Ammonium formate → HCID 10638671, compound

HRID 369425Notes

Reaction equation

HRID 369425 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][CH:30]=1)[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][CH:17]=[CH:16][C:15]=2[C:23]([O:25][CH2:26][CH3:27])=[O:24])C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[C].[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][CH:30]=1)[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][CH:17]=[CH:16][C:15]=2[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10548984HCID 10548984, compound

Product 1

HCID 10638671HCID 10638671, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

3'-Benzyloxy-8-ethoxycarbonylflavone (1 eq.) was dissolved in methanol, followed by the addition of ammonium formate (8 eq.) and 10% wt/wt palladium-carbon. The resulting mixture was refluxed. Subsequent to the completion of the reaction, the catalyst was eliminated by hot filtration. The mother liquor was allowed to cool down to room temperature. The resulting crystals were collected by filtration, washed with water and then recrystallized from DMF-ethanol, whereby the title compound was obtained (yield: 51%).

Workup

  1. temperatureThe resulting mixture was refluxed
  2. customSubsequent to the completion of the reaction
  3. filtrationthe catalyst was eliminated by hot filtration
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with water
  6. customrecrystallized from DMF-ethanol, whereby the title compound
  7. customwas obtained (yield: 51%)

Sources & evidence

ORD record
ord-7daae5117ee24cd585b913e4b4278c1d
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

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