Sulfuric Acid → HCID 18568651, compound

HRID 386668Notes

Reaction equation

HRID 386668 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:19]=[CH:18][C:17]([NH:20]C(=O)C)=[CH:16][C:12]=3[C:13](=[O:15])[CH:14]=2)=[CH:5][CH:4]=1.OS(O)(=O)=O.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:12]=3[C:13](=[O:15])[CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 16825909HCID 16825909, compound

Product 1

HCID 18568651HCID 18568651, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(4-methoxyphenyl)-6-acetamido-4H-1-benzopyran-4-one, 5 g (0.016 mol) in ethanol (solution 80% in water) (70 mL) was added H2SO4 30% (25 mL) and the mixture was stirred under reflux for 4 hours. After cooling, aqueous NaOH was added until pH 10, and the mixture was extracted with dichloromethane, washed with water, dried and evaporated. Yield: 97%; TLC (85/25/2/1 Chloroform/Methanol/Water/Ammonia) Rf: 0.82.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with dichloromethane
  4. washwashed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-06db7d00428842b29c8f31ce8d451009
Source dataset
uspto-grants-2013_02
Patent number
US08372866B2

Reaction notes

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