Sodium Hydroxide → 3-Cyclopentylidenemethylquinoline

HRID 5910Notes

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

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 aqueous sodium hydroxide solution (2M, 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 mmHg) 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 mmHg) afforded 3-cyclopentylidenemethylquinoline (4 g, 31 mmol) which was used without further purification;

Workup

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

Sources & evidence

ORD record: ord-f209a340a88445cc9ebe2dd704042b53
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246950

Reaction notes

Loading…