Pyridine → HCID 57890277, compound

HRID 644152Notes

Reaction equation

HRID 644152 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20](=[O:21])[C:19]3[C:14](=[C:15]([CH3:23])[C:16]([OH:22])=[CH:17][CH:18]=3)[O:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].N1C=CC=CC=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>>[C:30]([O:22][C:16]1[C:15]([CH3:23])=[C:14]2[C:19]([C:20](=[O:21])[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:12][O:13]2)=[CH:18][CH:17]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 21270165HCID 21270165, compound

Product 1

HCID 57890277HCID 57890277, compoundYield 42%

Conditions

Temperature
-18 °C

Procedure

3-(3,4-Dimethoxy-phenyl)-7-hydroxy-8-methylchromen-4-one (94.8 g) was suspended in acetic anhydride (450 mL) under a nitrogen atmosphere. Pyridine (23 mL) was added and the reaction mixture was heated to reflux for 1 hour. The pot was cooled overnight at −18° C. to produce a crystalline solid within the reaction mixture. This was filtered and the solid was washed with the filtrate and additional water (500 mL) to yield a brown solid. Further washing with ethanol produced a white crystalline solid. The solid was dried overnight in a desiccator to yield 7-acetoxy-3-(3,4-dimethoxyphenyl)-8-methylchromen-4-one (44.7 g, 42%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. customto produce a crystalline solid within the reaction mixture
  4. filtrationThis was filtered
  5. washthe solid was washed with the filtrate and additional water (500 mL)
  6. customto yield a brown solid
  7. washFurther washing with ethanol
  8. customproduced a white crystalline solid
  9. customThe solid was dried overnight in a desiccator

Sources & evidence

ORD record
ord-10fe1bb152f142d4a1447397fb6d0f55
Source dataset
uspto-grants-2010_04
Patent number
US07700644B2

Reaction notes

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