p-Toluenesulfonic acid → HCID 18673936, compound

HRID 1635978Notes

Reaction equation

HRID 1635978 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][CH2:14][C:15]3=[O:20])=[N:8][CH:9]=1)([O-:3])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:32](OC(C)=C)(=[O:34])[CH3:33]>>[C:32]([O:20][C:15]1[C:16]2[C:12](=[C:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=3)[CH:19]=[CH:18][CH:17]=2)[CH2:13][CH:14]=1)(=[O:34])[CH3:33]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7916Isopropenyl acetateHCID 18673889HCID 18673889, compound

Product 1

HCID 18673936HCID 18673936, compound

Conditions

Temperature
80 °C

Procedure

To 5.00 g of 4-[(5-nitro-2-piridinyl)oxy]-1-indanone, 10 ml of isopropenyl acetate and 70 mg of p-toluenesulfonic acid were added and the mixture was stirred at 80° C. After 7.5 hours, the reaction solution was concentrated under reduced pressure. To the resulting residue, ethyl acetate was added and the solution was washed in turn with a saturated sodium hydrogencarbonate solution and a saturated sodium chloride solution. The solution extracted with ethyl acetate was dried over anhydrous magnesium sulfate and the solvent was distilled off. The resulting residue was washed with isopropyl ether in a hot state to obtain 4.70 g of the titled compound.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. additionTo the resulting residue, ethyl acetate was added
  3. washthe solution was washed in turn with a saturated sodium hydrogencarbonate solution
  4. extractionThe solution extracted with ethyl acetate
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. washThe resulting residue was washed with isopropyl ether in a hot state

Sources & evidence

ORD record
ord-287713932edf4a829ab17731006c453c
Source dataset
uspto-grants-2003_01
Patent number
US06511995B1

Reaction notes

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