Sulfuric Acid → 2-(benzo[1,3]dioxol-5-yl)-3-hydroxy-6-amino-4H-1-benzopyran-4-one

HRID 2301346Notes

Reaction equation

HRID 2301346 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:12]4[C:17]([C:18](=[O:21])[C:19]=3[OH:20])=[CH:16][C:15]([NH:22]C(=O)C)=[CH:14][CH:13]=4)=[CH:9][C:4]=2[O:3][CH2:2]1.S(=O)(=O)(O)O.O.N>C(O)C>[NH2:22][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[O:11][C:10]([C:8]1[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=1)=[C:19]([OH:20])[C:18]2=[O:21]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 9949777HCID 9949777, compoundHCID 12896473Azane;hydrate

Product 1

HCID 99262072-(benzo[1,3]dioxol-5-yl)-3-hydroxy-6-amino-4H-1-benzopyran-4-oneYield 68.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3 g (8.85 mmol) of the compound obtained in Example 23 was stirred in 30 ml of aqueous 80% ethanol solution and 10 ml of aqueous 30% sulfuric acid solution at 120° C. for 18 hours. After the reaction was completed, the mixture was cooled to room temperature, and neutralized with conc. ammonia water. Then the obtained solid was filtered, washed with water, and dried to give 1.8 g of the title compound in a yield of 68%.

Workup

  1. filtrationThen the obtained solid was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-d9111ef174cd44aa9c1838f59cc87aa0
Source dataset
uspto-grants-2002_12
Patent number
US06500846B1

Reaction notes

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