Sulfuric Acid → HCID 5327028, compound

HRID 1904705Notes

Reaction equation

HRID 1904705 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14](O)[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.OS(O)(=O)=O>CC(O)=O>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 3655Velnacrine

Product 1

HCID 5327028HCID 5327028, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 50 ml of HOAc was dissolved 3.00 g of 9-amino-1,2,3,4-tetrahydroacridin-1-ol. To this mechanically stirred solution at room temperature was added 0.75 ml (1 eq) of H2SO4. The reaction mixture was warmed on a steam bath causing a precipitate to form. After 0.5 hour of heating, the reaction was complete based on thin layer chromatography. The reaction mixture was poured into excess ice/10% NaOH and the precipitate was collected. The precipitate was dissolved in dichloromethane, dried over MgSO4, filtered, and evaporated to a solid which was purified by silica gel chromatography to yield a solid. Two recrystallizations from dichloromethane/hexanes yielded 1.40 g (52%) of a powder, melting point 178°-179° C.

Workup

  1. temperatureThe reaction mixture was warmed on a steam bath
  2. customto form
  3. temperatureAfter 0.5 hour of heating
  4. customthe precipitate was collected
  5. dissolutionThe precipitate was dissolved in dichloromethane
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to a solid which
  9. customwas purified by silica gel chromatography
  10. customto yield a solid
  11. customTwo recrystallizations from dichloromethane/hexanes

Sources & evidence

ORD record
ord-14f0d2ea1eb947278065d6263c4f1c19
Source dataset
uspto-grants-1989_06
Patent number
US04839364

Reaction notes

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