Sodium Hydroxide → 3-Cyclopentylidenemethylquinoline

HRID 1886376Notes

Reaction equation

HRID 1886376 reaction equation
Cl[C:2]1[C:11]([CH:12]=[C:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH-].[Na+]>C(O)(=O)C.[Zn]>[C:13]1(=[CH:12][C:11]2[CH:2]=[N:3][C:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19794617HCID 19794617, compound

Product 1

HCID 197945743-CyclopentylidenemethylquinolineYield 99%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-chloro-3-cyclopentylidenemethylquinoline (7.6 g, 31.3 mmol) in glacial acetic acid (80 ml) at 60° C. was treated with zinc powder (4.0 g, 62.6 mmol). After stirring at 60° C. for 3 hours, the reaction mixture was cooled and then treated dropwise with 2M aqueous sodium hydroxide solution (330 ml); the temperature being kept below 20° C. throughout. The resulting mixture was then extracted with ethyl acetate (2×250 ml). The combined organic extracts were dried over sodium sulphate then concentrated in vacuo (30° C., 14 mm Hg) to give a crude red oil (8 g) which was extracted with hot pentane (2×200 ml). Concentration of the combined extracts in vacuo (20° C., 14 mm Hg) afforded 3-cyclopentylidenemethylquinoline (4 g, 31 mmol) which was used without further purification N.M.R. (CDCl3) 1.6-1.96 (m, 4H); 2.5-2.72 (m, 4H); 6.50 (m, 1H), 7.46-7.58 (ddd, 1H) 7.60-7.68 (ddd, 1H), 7.76-7.80 (dd, 1H); 8.0-8.08 (c, 2H).

Workup

  1. temperaturethe reaction mixture was cooled
  2. custombeing kept below 20° C.
  3. extractionThe resulting mixture was then extracted with ethyl acetate (2×250 ml)
  4. dry with materialThe combined organic extracts were dried over sodium sulphate
  5. concentrationthen concentrated in vacuo (30° C., 14 mm Hg)
  6. customto give a crude red oil (8 g) which
  7. extractionwas extracted with hot pentane (2×200 ml)

Sources & evidence

ORD record
ord-4990ba8a8de244298399cbd79d4dda3c
Source dataset
uspto-grants-1992_09
Patent number
US05151436

Reaction notes

Loading…