Potassium Carbonate → Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-cyclopropylmethyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 4562

Reaction equation

HRID 4562 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]=[CH:7][C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]2[OH:22].C(=O)([O-])[O-].[K+].[K+].[CH:29]1([CH2:32]Br)[CH2:31][CH2:30]1>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([CH2:32][CH:29]1[CH2:31][CH2:30]1)[CH:7]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 178418515HCID 178418515, compound

Product 1

HCID 13670064Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-cyclopropylmethyl-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.6 g (0.012 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-carboxylate and 4.15 g (0.03 mol) of potassium carbonate in 30 ml of dimethlformamide is heated for 30 minutes at 80° C. and left to cool, 8 g (0.06 mol) of cyclopropylmethyl bromide are added, the mixture is kept for 12 hours at 90° C. and left to cool, 80 ml of a water/ice mixture are added and the precipitate formed is filtered off, washed with water and recrystallized from ethanol to give 2.65 g of a solid melting at 125°-127° C.

Workup

  1. waitleft
  2. temperatureto cool
  3. waitleft
  4. temperatureto cool
  5. customthe precipitate formed
  6. filtrationis filtered off
  7. washwashed with water
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-fd0d21daeb32407586c452e4c390cba8
Source dataset
uspto-grants-1988_02
Patent number
US04727080

Linked notes

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