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

HRID 4565

Reaction equation

HRID 4565 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+].[N+:29](C1C=C([N+]([O-])=O)C=CC=1NO)([O-])=O>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]([NH2:29])[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 5743493N-Hydroxy-2,4-dinitrobenzenamineHCID 178418515HCID 178418515, compound

Product 1

HCID 13670072Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-amino-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 23.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6 g (0.02 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-carboxylate and 5.6 g (0.04 mol) of potassium carbonate in 80 ml of dimethylformamide is heated for 30 minutes at 60° C. and left to cool, 8.5 g (0.042 mol) of 2,4-dinitrophenylhydroxylamine are added, the mixture is kept for 24 hours at room temperature and poured into 200 ml of a water/ice mixture, and the precipitate formed is filtered off, washed with water, dried in a desiccator and recrystallized from dimethylformamide to give 1.5 g of a solid melting at 276°-279° C.

Workup

  1. waitleft
  2. temperatureto cool
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washwashed with water
  6. customdried in a desiccator
  7. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-26cbc7a835c94c10aedfdc353735302f
Source dataset
uspto-grants-1988_02
Patent number
US04727080

Linked notes

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