Acetic Acid → HCID 22100389, compound

HRID 1457774Notes

Reaction equation

HRID 1457774 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:12][C:11]([CH2:13][CH2:14][CH2:15][CH3:16])=[N:10][C:5]2=[N+:6]([O-])[C:7]=1[CH3:8].C(O)(=[O:19])C>>[Br:1][C:2]1[CH:3]=[C:4]2[NH:12][C:11]([CH2:13][CH2:14][CH2:15][CH3:16])=[N:10][C:5]2=[N:6][C:7]=1[CH2:8][OH:19]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 178441440HCID 178441440, compound

Product 1

HCID 22100389HCID 22100389, compoundYield 66%

Conditions

Temperature
120 °C

Procedure

8.0 g (0.02817 mole) of the compound obtained in step 5 was dissolved in 20 ml of anhydrous acetic acid. The resulting solution was stirred for 1 hour at 120° C., and evaporated under reduced pressure to remove anhydrous acetic acid. Thereafter, the residue was dissolved in a mixture of 30 ml of methanol and 40 ml of 3N LiOH. The resulting solution was refluxed for 1 hour, evaporated under reduced pressure to remove methanol, neutralized with 1N HCl and extracted with ethyl acetate(50 ml×3). The organic layer was dried over Na2SO4. The residue was concentrated under reduced pressure and purified with column chromatography(hexane:ethyl acetate =1:2) to obtain 5.3 g of the title compound(yield 66%).

Workup

  1. customevaporated under reduced pressure
  2. customto remove anhydrous acetic acid
  3. dissolutionThereafter, the residue was dissolved in a mixture of 30 ml of methanol and 40 ml of 3N LiOH
  4. temperatureThe resulting solution was refluxed for 1 hour
  5. customevaporated under reduced pressure
  6. customto remove methanol
  7. extractionextracted with ethyl acetate(50 ml×3)
  8. dry with materialThe organic layer was dried over Na2SO4
  9. concentrationThe residue was concentrated under reduced pressure
  10. custompurified with column chromatography(hexane:ethyl acetate =1:2)

Sources & evidence

ORD record
ord-4335dcdf1d6b413d8bde60f0df1303ba
Source dataset
uspto-grants-1998_12
Patent number
US05849753

Reaction notes

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