Hydrochloric Acid → Ethyl 6H-pyrido[3,2,1-de]acridin-1(2H)-one

HRID 54923Notes

Reaction equation

HRID 54923 reaction equation
[O-][CH2:2][CH3:3].[Na+].[C:5]1(=[O:22])[N:20]2[C:21]3[C:12](=[CH:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=42)[CH2:11][CH:10]=[CH:9][C:8]=3[CH2:7][CH2:6]1.C(=O)(OCC)OCC.Cl>C(O)C>[CH2:2]([CH:6]1[C:5](=[O:22])[N:20]2[C:21]3[C:12](=[CH:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=42)[CH2:11][CH:10]=[CH:9][C:8]=3[CH2:7]1)[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 2723922Sodium ethoxideHCID 677259016H-pyrido[3,2,1-de]acridin-1(2H)-one

Product 1

HCID 67724926Ethyl 6H-pyrido[3,2,1-de]acridin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a freshly prepared solution of sodium ethoxide in ethanol (from 0.35 g sodium metal and 10 ml ethanol) was added 6H-pyrido[3,2,1-de]acridin-1(2H)-one (1.2 g) portionwise over a period of 10 minutes. To the resulting dark red solution was slowly added diethyl carbonate (1.77 g) and the solution was then refluxed for 3 hours. The reaction mixture was cooled, acidified to pH 2 with concentrated HCl and then extracted with methylene chloride. The organic extract was washed with water and was then collected, dried and evaporated to dryness to obtain a light amber solid (1.8 g; m.p. 113°-118° C.).

Workup

  1. temperaturethe solution was then refluxed for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with methylene chloride
  4. extractionThe organic extract
  5. washwas washed with water
  6. customwas then collected
  7. customdried
  8. customevaporated to dryness
  9. customto obtain a light amber solid (1.8 g; m.p. 113°-118° C.)

Sources & evidence

ORD record
ord-e0d857e89cd04585803ccfc2a77737d0
Source dataset
uspto-grants-1997_04
Patent number
US05624929

Reaction notes

Loading…