Hydrochloric Acid → 1-(1-Methyl-3-indolyl)cyclopentanecarbaldehyde

HRID 1587715Notes

Reaction equation

HRID 1587715 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2([C:26]#N)[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:13]1.Cl.C([O:32]C(C)C)(C)C>C1(C)C=CC=CC=1.CO>[CH3:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2([CH:26]=[O:32])[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:13]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 107991831-(1-Methyl-3-indolyl)-cyclopentanecarbonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 105612721-(1-Methyl-3-indolyl)cyclopentanecarbaldehyde

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

The reaction is performed under a dry nitrogen atmosphere. 94.4 cm3 (0.0944 mol) of a 1N toluene solution of diisobutylaluminium hydride are added at -60° C. to a solution of 13.3 g (0.059 mol) of 1-(1-methyl-3-indolyl)-cyclopentanecarbonitrile in 230 cm3 of toluene. The temperature of the mixture is thereafter allowed to rise to room temperature, and the reaction is then stopped by adding 50 cm3 of methanol and then 230 cm3 of 3N hydrochloric acid to the reaction mixture. The mixture is extracted with dichloromethane, the organic extract is washed with water, dried over sodium sulphate and filtered and the filtrate is evaporated. In succession, the residue obtained is taken up with diisopropyl ether, some insoluble matter is removed by filtration, the solvent is evaporated and the residue is crystallised in hexane.

Workup

  1. customto rise to room temperature
  2. extractionThe mixture is extracted with dichloromethane
  3. extractionthe organic extract
  4. washis washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customthe filtrate is evaporated
  8. customIn succession, the residue obtained
  9. customsome insoluble matter is removed by filtration
  10. customthe solvent is evaporated
  11. customthe residue is crystallised in hexane

Sources & evidence

ORD record
ord-5f1f65eba6d24f2288154e47d358c821
Source dataset
uspto-grants-1993_06
Patent number
US05219859

Reaction notes

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