Acetic Acid → HCID 10663825, compound

HRID 275455Notes

Reaction equation

HRID 275455 reaction equation
[C:1]1([NH:7][C:8]([C:10]2([CH3:27])[CH2:15][CH2:14][C:13]3[C:16]([CH3:26])=[C:17]([O:22]C(=O)C)[C:18]([CH3:21])=[C:19]([CH3:20])[C:12]=3[O:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C(O)(=O)C>C(O)C.O>[C:1]1([NH:7][C:8]([C:10]2([CH3:27])[CH2:15][CH2:14][C:13]3[C:16]([CH3:26])=[C:17]([OH:22])[C:18]([CH3:21])=[C:19]([CH3:20])[C:12]=3[O:11]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 10642727HCID 10642727, compound

Product 1

HCID 10663825HCID 10663825, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a two-necked, round-bottomed flask, 2.75 g (7.48 mmol) of the compound obtained in Stage B of Example 1 are dissolved in 60 cm3 of 80 % ethanol. Under a nitrogen stream, 18 cm3 of 2.5N sodium hydroxide are added. The mixture is left to stir at ordinary temperature for 2 h. The mixture is diluted with water, acidified with acetic acid and then the product is extracted with dichloromethane. The organic phase is washed with water and then dried. The mixture is purified by passing through a column of silica gel, eluting with isopropyl ether to obtain N-phenyl-6-hydroxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxamide (yield: 86 %; melting point: 107°-109° C.) and then the reaction is carried out as in Stage C of Example 1, replacing N-phenyl-6-acetoxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxamide with N-phenyl-6-hydroxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxamide.

Workup

  1. waitThe mixture is left
  2. extractionthe product is extracted with dichloromethane
  3. washThe organic phase is washed with water
  4. customdried
  5. customThe mixture is purified
  6. washeluting with isopropyl ether

Sources & evidence

ORD record
ord-211dc0d8d4ab43738b20da37491f00ae
Source dataset
uspto-grants-1995_02
Patent number
US05393775

Reaction notes

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