Aluminum(III) Chloride → HCID 209436, compound

HRID 1730385Notes

Reaction equation

HRID 1730385 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:11]([CH:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH:17]=[CH:16][C:15]2[CH:24]=[CH:25][CH:26]=[CH:27][C:14]1=2)#[N:12]>CCOCC>[NH2:12][CH2:11][CH:13]1[C:14]2[CH:27]=[CH:26][CH:25]=[CH:24][C:15]=2[CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]1=2

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 14950891HCID 14950891, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 209436HCID 209436, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of anhydrous aluminum chloride (6.21 g., 0.0466 mole) in 75 ml. of anhydrous ether is added dropwise to a solution of lithium aluminum hydride (1.77 g., 0.0466 mole) in 50 ml. of absolute ether while stirring.An atmosphere of nitrogen is maintained in the apparatus and all vents are protected with drying tubes during the reaction. A solution of 5-cyano-5H-dibenzo[a,d]cycloheptene (10.13 g., 0.0466 mole) in 250 ml. of absolute ether is added dropwise with stirring (occasional warming of thissolution may be necessary to prevent precipitation of the nitrile). The reaction mixture is stirred at 23-26° C. for 1 hour after the addition is complete. Water, 35 ml., then is added dropwise. Dilute sulfuric acid is added, causing precipitation of a white solid. The solid is collected, suspended in water and the mixture rendered strongly alkaline with sodium hydroxide solution. The filtrate also is rendered strongly alkaline and both mixtures, containing suspended solids are extracted separately with ether. Distillation of the ether from the combined extracts leaves a white solid residue, m.p. 95°-96.5° C., weighing 10.04 g. Recrystallization from hexane gives 8.71 g. of product, m.p. 97.5°-98.3° C. (sinters 97° C.). An analytical sample melts at 98-98.8° C. (sinters 97° C.).

Workup

  1. customall vents are protected with drying tubes during the reaction
  2. temperatureoccasional warming of thissolution
  3. customprecipitation of the nitrile)
  4. stirringThe reaction mixture is stirred at 23-26° C. for 1 hour
  5. additionafter the addition
  6. addition, then is added dropwise
  7. additionDilute sulfuric acid is added
  8. customprecipitation of a white solid
  9. customThe solid is collected
  10. additionboth mixtures, containing
  11. extractionare extracted separately with ether
  12. distillationDistillation of the ether from the combined extracts
  13. customleaves a white solid residue, m.p. 95°-96.5° C.
  14. customRecrystallization from hexane
  15. customgives 8.71 g
  16. customof product, m.p. 97.5°-98.3° C. (sinters 97° C.)
  17. customAn analytical sample melts at 98-98.8° C. (sinters 97° C.)

Sources & evidence

ORD record
ord-93923d1b1e034448a9a2082f0c553b51
Source dataset
uspto-grants-1976_11
Patent number
US03992445

Reaction notes

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