Methanol → HCID 373774, compound

HRID 1086617Notes

Reaction equation

HRID 1086617 reaction equation
[CH2:1]([C:5]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[N:12]=[C:13]2[C:18]=1[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:2][CH2:3][CH3:4].[OH:19]OS([O-])=O.[K+].C([O-])(O)=O.[Na+].CO>O>[CH2:1]([C:5]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[N+:12]([O-:19])=[C:13]2[C:18]=1[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 10890121Acridine, 9-butyl-1,2,3,4,5,6,7,8-octahydro-HCID 23707502Potassium hydroxy sulfite

Product 1

HCID 373774HCID 373774, compoundYield 125.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
47.5 °C

Procedure

Into a 2L round-bottomed flask equipped with a magnetic stirrer and a reflux condenser fitted with a nitrogen inlet are placed 38.0 g (0.16 mol) of 9-n-butyl-1,2,3,4,5, 6,7,8-octahydroacridine, 72.0 g (0.12 mol) of Oxone (Note 9), 28.5 g (0.34 mol) of NaHCO3, 790 mL of methanol and 240 mL of water. The resulting suspension is stirred at 45-50° C. in an atmosphere of nitrogen for 24 hrs. (Note 10). The cooled reaction mixture is vacuum filtered, washing the residual salts with methanol (2×50 mL). The methanol is removed from the combined filtrates by means of a rotary evaporator and the resulting mixture is extracted with methylene chloride (3× 100 mL). The combined extracts are washed with water (2×50 mL), dried using anhydrous magnesium sulfate and concentrated to dryness by means of a rotary evaporator. Residual solvent is removed at 0.1 mm, yielding 39 g (96%) of 9-n-butyl-1,2,3,4,5,6,7,8-octahydroacridine-N-oxide as a pale yellow solid, mp 89-92° C. (Note 11).

Workup

  1. customfitted with a nitrogen inlet
  2. customThe cooled reaction mixture
  3. filtrationfiltered
  4. washwashing the residual salts with methanol (2×50 mL)
  5. customThe methanol is removed from the combined filtrates by means of a rotary evaporator
  6. extractionthe resulting mixture is extracted with methylene chloride (3× 100 mL)
  7. washThe combined extracts are washed with water (2×50 mL)
  8. customdried
  9. concentrationconcentrated to dryness by means of a rotary evaporator
  10. customResidual solvent is removed at 0.1 mm

Sources & evidence

ORD record
ord-f02cf06a90e04d14beacf88184793297
Source dataset
uspto-grants-1991_07
Patent number
US05030728

Reaction notes

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