تفاعل #4881

معادلة التفاعل

diisopropyl amine

n-butyllithium

hexane

2-chloroquinoline

dry ice

→

white crystals

المردود 62.0%

2-Chloro-3-quinolinecarboxylic acid

المردود 62.0%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwhile maintaining the temperature at -60° to -70° C
2. 2
   workup.ADDITIONSubsequent to this addition
3. 3
   درجة الحرارةwhile maintaining the temperature at -60° to -70° C
4. 4
   أخرىat -65° C.
5. 5
   أخرىfor 20 minutes
6. 6
   workup.ADDITIONsubsequent to this addition
7. 7
   أخرىthe entire reaction mixture
8. 8
   أخرىMost of the solvent was evaporated in a stream of air
9. 9
   أخرىthe residual solvent was removed by rotary evaporation
10. 10
    غسيلwashed with 3×50 ml of isopropyl ether
11. 11
    ترشيحThe aqueous layer was filtered
12. 12
    أخرىThe precipitate was collected
13. 13
    غسيلwashed with water, isopropyl alcohol, and isopropyl ether
14. 14
    أخرىdried

الإجراء التجريبي

To a solution of 21.3 ml (0.15 mole) of diisopropyl amine in 300 ml of dry tetrahydrofuran under a continuous nitrogen blanket, at -70° C., was added 61.6 ml of 2.7M n-butyllithium in hexane (0.165 mole) while maintaining the temperature at -60° to -70° C. Subsequent to this addition, the temperature was maintained at -65° C. for approximately 20 minutes. A solution of 20 g (0.12 mole) of 2-chloroquinoline in 60 ml of tetrahydrofuran was added dropwise while maintaining the temperature at -60° to -70° C. After holding the temperature at -65° C. for 20 minutes subsequent to this addition, the entire reaction mixture was poured onto a large excess of dry ice. Most of the solvent was evaporated in a stream of air; the residual solvent was removed by rotary evaporation. The residue was taken up in 300 ml water, made basic with dil aq. sodium hydroxide and washed with 3×50 ml of isopropyl ether. The aqueous layer was filtered and made acidic (4 to 5 pH) with dilute aqueous hydrochloric acid. The precipitate was collected, washed with water, isopropyl alcohol, and isopropyl ether, and dried, giving 15.4 g (62%) of white crystals, m.p. 190°-210° C. (decomp.). A sample was recrystallized from isopropyl alcohol giving an analytical sample, m.p. 190°-210° C. (decomp.).

المصدر