Sulfuric Acid → HCID 67947754, compound

HRID 1249413Notes

Reaction equation

HRID 1249413 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]([OH:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.OS(O)(=O)=O>CC(O)=O>[OH2:16].[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.[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 67947754HCID 67947754, compound

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 (75% crude yield prior to chromatography) 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
  12. customyielded 1.40 g (75% crude yield

Sources & evidence

ORD record
ord-65ab75619b734eeea66a428f95f3e49d
Source dataset
uspto-grants-1986_12
Patent number
US04631286

Reaction notes

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