Hydrochloric Acid → HCID 89853721, compound

HRID 931079Notes

Reaction equation

HRID 931079 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:12]#[N:13])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[ClH:14].[CH2:15]([OH:17])C>CO>[ClH:14].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:12](=[NH:13])[O:17][CH3:15])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 510639591-(3-Methoxyphenyl)cyclopropane-1-carbonitrile

Product 1

HCID 89853721HCID 89853721, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(3-Methoxyphenyl)cyclopropanecarbonitrile (56 mg, 0.32 mmol) was dissolved into a saturated solution of hydrogen chloride in ethanol (1 mL). The reaction mixture was stored in the refrigerator (4° C.) for three days. The reaction mixture was concentrated under reduced pressure and dried under high vacuum. The residue was dissolved in ethanol (0.5 mL) and silica sulfuric acid (125 mg), prepared by following the literature (Tetrahedron, 2001, 57, 9509-9511), was added. The reaction mixture was stirred at room temperature for 2 h. The silica was filtered off and the filtrate was cooled to 0° C. and gaseous hydrogen chloride was bubbled through the solution for 30 seconds. The reaction mixture was stirred at room temperature for 18 h. The mixture was concentrated under reduced pressure to give an oil. The oil was dissolved into a solution of hydrogen chloride in methanol (1.25 M, 1 mL). Gaseous hydrochloric acid was bubbled into the solution and the mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure to afford the title compound as an oil (40 mg, 51%). The material was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customdried under high vacuum
  3. dissolutionThe residue was dissolved in ethanol (0.5 mL)
  4. customsilica sulfuric acid (125 mg), prepared
  5. additionwas added
  6. filtrationThe silica was filtered off
  7. temperaturethe filtrate was cooled to 0° C.
  8. customgaseous hydrogen chloride was bubbled through the solution for 30 seconds
  9. stirringThe reaction mixture was stirred at room temperature for 18 h
  10. concentrationThe mixture was concentrated under reduced pressure
  11. customto give an oil
  12. customGaseous hydrochloric acid was bubbled into the solution
  13. stirringthe mixture was stirred at room temperature for 18 h
  14. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f6d721ad158f47caa97867116b0b9fe2
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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