Pyrrolidine → HCID 11557630, compound

HRID 2107312Notes

Reaction equation

HRID 2107312 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>C(OCCO)C>[N:14]1([C:2]2[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]3)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 14839464HCID 14839464, compound

Product 1

HCID 11557630HCID 11557630, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

5-Chloro-8-nitroquinoline, 5 g, was reduced, diazonized, and cyanized in the same manner as in Example 1 to produce 2.62 g (yield: 58%) of 5-chloro-8-quinolinecarbonitrile. A mixture of 1.88 g of 5-chloro-8-quinolinecarbonitrile thus prepared and 7.10 g of pyrrolidine was dissolved into 30 ml of 2-ethoxyethanol and the solution was heated under reflux for 3 hours. The solvent was evaporated, and the residue, after addition of water, was extracted with chloroform. The extract was washed with water and dried over anhydrous sodium sulfate. Chloroform was evaporated, and the residue was refined by column chromatography on silica gel using a chloroform-methanol (95:5) mixed solvent as an eluent. The crystals thus obtained were recrystallized from ethanol to yield 1.54 g (yield: 69%) of 5-pyrrolidino-8-quinolinecarbonitrile (Compound No. 7).

Workup

  1. customthus prepared
  2. temperaturethe solution was heated
  3. temperatureunder reflux for 3 hours
  4. customThe solvent was evaporated
  5. additionthe residue, after addition of water
  6. extractionwas extracted with chloroform
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customChloroform was evaporated
  10. additionmixed solvent as an eluent
  11. customThe crystals thus obtained
  12. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-ac8373230c7646faad9cb483f40b9a3d
Source dataset
uspto-grants-1990_06
Patent number
US04933447

Reaction notes

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