Ethanol → HCID 12813958, compound

HRID 1076511Notes

Reaction equation

HRID 1076511 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([CH:15]=1)=[N+:13]([CH3:16])[C:12]1[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:6]=2[C:17]([O:19][CH3:20])=[O:18].C(O)C.[BH4-].[K+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]([C:17]([O:19][CH3:20])=[O:18])[C:7]3[C:12]([N:13]([CH3:16])[C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

5

Reactant 3

HCID 702EthanolHCID 4192641Potassium borohydrideHCID 12814002HCID 12814002, compound

Product 1

HCID 12813958HCID 12813958, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

5.3 gm of the methosulfate of 3-chloro-9-methoxycarbonyl-10-methyl-acridinium were added to a mixture of 50 cc of ethanol and 2.5 cc of water and after the addition of 5.3 gm potassium borohydride while maintaining a 25°C temperature, the mixture was stirred for 30 minutes and poured into water. After stirring for 30 minutes, the mixture was extracted with ether and the ether phase was washed with water, dried over magnesium sulfate and distilled to dryness in vacuo. The residue was dissolved in 30 cc of refluxing isopropyl ether, filtered and concentrated to 20 cc. The mixture was iced for 30 minutes and filtered. The precipitate was washed with iced isopropyl ether and dried in vacuo to obtain 3.18 gm of 3-chloro-9-methoxycarbonyl-10-methyl-acridane which was used as is for the next step.

Workup

  1. stirringAfter stirring for 30 minutes
  2. extractionthe mixture was extracted with ether
  3. washthe ether phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationdistilled to dryness in vacuo
  6. dissolutionThe residue was dissolved in 30 cc of refluxing isopropyl ether
  7. filtrationfiltered
  8. concentrationconcentrated to 20 cc
  9. waitThe mixture was iced for 30 minutes
  10. filtrationfiltered
  11. washThe precipitate was washed with iced isopropyl ether
  12. customdried in vacuo

Sources & evidence

ORD record
ord-c0b83b4d63ca433fa116eda43b5d5697
Source dataset
uspto-grants-1976_05
Patent number
US03957757

Reaction notes

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