تفاعل #4656

ord-d71e37624aff4110a72e833bc5f49268

معادلة التفاعل

CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O
ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-caboxylate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
OCCBr
ethylene bromohydrin
CCOC(=O)c1cn(CCO)c2cc(-n3cccc3)c(F)cc2c1=O
solid
المردود 45.9%
CCOC(=O)c1cn(CCO)c2cc(-n3cccc3)c(F)cc2c1=O
ethyl 6-fluoro-7-(pyrrol-1-yl)-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
المردود 45.9%

المذيبات

ظروف التفاعل

درجة الحرارة
60°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.WAITleft
  2. 2
    درجة الحرارةto cool
  3. 3
    درجة الحرارةthe mixture is heated at 80°-90° C. for 10 hours
  4. 4
    workup.ADDITIONactive carbon is added
  5. 5
    ترشيحthe mixture is filtered hot
  6. 6
    أخرىthe filtrate is evaporated to dryness, water
  7. 7
    workup.ADDITIONis added
  8. 8
    أخرىthe precipitate formed
  9. 9
    ترشيحis filtered off
  10. 10
    غسيلwashed with water
  11. 11
    أخرىIt is recrystallized from dimethylformamide

الإجراء التجريبي

A mixture of 2 g (0.0076 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-caboxylate and 1.85 g (2×0.0076 mol) of potassium carbonate in 20 ml of dimethylformamide is heated for 30 minutes at 60° C. and left to cool, 3.35 g (4×0.0076 mol) of ethylene bromohydrin are added, the mixture is heated at 80°-90° C. for 10 hours, active carbon is added, the mixture is filtered hot, the filtrate is evaporated to dryness, water is added and the precipitate formed is filtered off and washed with water. It is recrystallized from dimethylformamide to give 1.2 g of a solid melting at 237°-239° C.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04727080uspto-grants-1988_02