Water → HCID 12813969, compound

HRID 1076512Notes

Reaction equation

HRID 1076512 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]([C:28](OC)=[O:29])([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:13]3[C:18]([N:19]([CH3:22])[C:20]=2[CH:21]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3.O>O1CCCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]([CH2:28][OH:29])([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:13]3[C:18]([N:19]([CH3:22])[C:20]=2[CH:21]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3

Participants

5

Reactant 3

HCID 962WaterHCID 12813963HCID 12813963, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12813969HCID 12813969, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

25.7 gm of the fumarate of 3-chloro-9-methoxy-carbonyl-9-(β-dimethylaminoethyl)-10-methyl-acridane were suspended in 250 cc of water and after refrigeration, 25 cc of sodium hydroxide solution were added. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried over magnesium sulfate and distilled to dryness in vacuo to obtain 20 gm of 3-chloro-9-methoxycarbonyl-9-(β -dimethylaminoethyl)-10-methylacridane. First 10 gm of lithium aluminum hydride and then 20 gm of 3-chloro-9-methoxycarbonyl-9-(β-dimethylaminoethyl)-10-methylacridane in solution in 200 cc of tetrahydrofuran were added to 200 cc of cold tetrahydrofuran at a temperature below 10°C and after stirring for 10 minutes at 0°C, it was refluxed for 15 minutes. After cooling the reaction mixture, excess reactants were decomposed by 200 cc of tetrahydrofuran containing 20% of water at a temperature below 10°C. After filtering and distilling the mixture to dryness in vacuo, the residue was dissolved in methylene chloride and the solution was washed with water, dried over magnesium sulfate and distilled to dryness in vacuo. The residue was dissolved in 80 cc of ethyl acetate and the resulting solution was filtered and concentrated to 50 cc after which crystallization began. After being iced for 30 minutes, the mixture was filtered and the precipitate was washed with ethyl acetate and then ether and dried to obtain 14.35 gm of 3-chloro-9-hydroxymethyl-9-(β-dimethylaminoethyl)-10-methyl-acridane melting at 120°C.

Workup

  1. temperatureit was refluxed for 15 minutes
  2. temperatureAfter cooling the reaction mixture, excess reactants
  3. filtrationAfter filtering
  4. distillationdistilling the mixture to dryness in vacuo
  5. dissolutionthe residue was dissolved in methylene chloride
  6. washthe solution was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationdistilled to dryness in vacuo
  9. dissolutionThe residue was dissolved in 80 cc of ethyl acetate
  10. filtrationthe resulting solution was filtered
  11. concentrationconcentrated to 50 cc
  12. customafter which crystallization
  13. waitAfter being iced for 30 minutes
  14. filtrationthe mixture was filtered
  15. washthe precipitate was washed with ethyl acetate
  16. dry with materialether and dried

Sources & evidence

ORD record
ord-ef795e8d7a374e75bd367a00bfd098ec
Source dataset
uspto-grants-1976_05
Patent number
US03957757

Reaction notes

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