تفاعل #586107

ord-3b3a2fff2a92436eadaf32b26bbb33a6

معادلة التفاعل

N
ammonia
CC1=C(c2cccc3cccnc23)CCC1(O)c1ccccc1
3-hydroxy-2-methyl-3-phenyl-1-(8-quinolyl)cyclopentene
O
water
Cl
hydrochloric acid
CC1=C(c2cccc3cccnc23)CC=C1c1ccccc1
2-methyl-3-phenyl-1-(8-quinolyl)cyclopentadiene
المردود 69.3%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe aqueous phase was then separated off from the organic phase
  2. 2
    استخلاصthe aqueous phase was extracted twice with diethyl ether
  3. 3
    تجفيفdried over magnesium sulfate
  4. 4
    ترشيحfiltered
  5. 5
    workup.DISTILLATIONthe solvent was distilled off
  6. 6
    أخرىThe residue obtained in this way
  7. 7
    workup.DISTILLATIONwas distilled at 157-170° C.

الإجراء التجريبي

A mixture of 5 ml of water and 5 ml of concentrated hydrochloric acid was added to a solution of 1.717 g (5.7 mmol) of 3-hydroxy-2-methyl-3-phenyl-1-(8-quinolyl)cyclopentene in 100 ml of tetrahydrofuran. The mixture was stirred at room temperature for 90 minutes and ammonia solution was then added until the pH was 12. The aqueous phase was then separated off from the organic phase and the aqueous phase was extracted twice with diethyl ether. The organic phases were combined, dried over magnesium sulfate, filtered and the solvent was distilled off. The residue obtained in this way was distilled at 157-170° C. and 2×10−2 mbar to give 1.12 g (3.95 mmol, 69.3%) of 2-methyl-3-phenyl-1-(8-quinolyl)cyclopentadiene.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07767613B2uspto-grants-2010_08