Hydrochloric Acid → HCID 21452728, compound

HRID 436512Notes

Reaction equation

HRID 436512 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9]C(C#N)CC[C:5]2=1.[O:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[CH3:22][Mg]I.Cl>O.CCOCC>[C:21]([CH:20]1[CH2:9][CH2:10][C:5]2[C:4]3[C:12](=[CH:13][CH:14]=[C:2]([Cl:1])[CH:3]=3)[NH:11][C:18]=2[CH2:19]1)(=[O:17])[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21452721HCID 21452721, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 21452728HCID 21452728, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 1.0 g. of 6-chloro-2-cyano-1,2,3,4-tetrahydrocarbazole in 15 ml. of tetrahydrofuran was added dropwise to a cooled (10° C. ), stirred solution of 9.6 g. of methyl magnesium iodide in 20 ml. of ether. The reaction mixture was refluxed and stirred under an atmosphere of dry nitrogen for 24 hours. Thereafter, it was cooled to 5° C. in an ice bath and 50 ml. of cold water was carefully added followed by 3 ml. of concentrated hydrochloric acid. The mixture was heated for 3 hours on a steam bath. After the mixture had been cooled by adding ice, it was extracted with ether. The ether solution was washed by extraction with dilute sodium bicarbonate and water. When the ether solution had dried over anhydrous magnesium sulfate, the desiccant was removed by filtration and the ether was removed by distillation, yielding 0.8 g.of product. Following crystallization from a mixture of hexane and ethyl acetate, 0.4 g. of 2-acetyl-6-chloro-1,2,3,4-tetrahydrocarbazole was obtained, m.p. 159° -161°.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. stirringstirred under an atmosphere of dry nitrogen for 24 hours
  3. temperatureThereafter, it was cooled to 5° C. in an ice bath
  4. temperatureThe mixture was heated for 3 hours on a steam bath
  5. temperatureAfter the mixture had been cooled
  6. additionby adding ice, it
  7. extractionwas extracted with ether
  8. washThe ether solution was washed by extraction with dilute sodium bicarbonate and water
  9. dry with materialWhen the ether solution had dried over anhydrous magnesium sulfate
  10. customthe desiccant was removed by filtration
  11. customthe ether was removed by distillation
  12. customyielding 0.8 g
  13. customcrystallization
  14. additionfrom a mixture of hexane and ethyl acetate, 0.4 g

Sources & evidence

ORD record
ord-753b9853595848f28d3d620d4976bfac
Source dataset
uspto-grants-1977_02
Patent number
US04009181

Reaction notes

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