Iodoethane → HCID 13309027, compound

HRID 615143Notes

Reaction equation

HRID 615143 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[NH:8][CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23].[H-].[Na+].[CH2:26](I)[CH3:27]>CN(C)C=O>[CH2:26]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([C:12]3[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=3)[N:10]=2)[C:5](=[O:23])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7]1)[CH3:27]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13309024HCID 13309024, compound

Product 1

HCID 13309027HCID 13309027, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 2.63 g of ethyl 6-fluoro-1,4-dihydro-4-oxo-7-(4-pyridyl)-1,8-naphthyridine-3-carboxylate, 0.42 g of 50% sodium hydride (dispersed in mineral oil) and 30 ml of dimethylformamide was heated at 50°-60° C. for 10 minutes. To the stirred mixture was added 1.31 g of ethyl iodide, and heating was continued for 1.5 hours. The reaction mixture was filtered and the filtrate was concentrated to dryness in vacuo and the residue was taken up in a mixture of chloroform and water. The chloroform layer was separated and the chloroform was evaporated in vacuo to give crystals which were recrystallized from ethyl acetate to yield ethyl 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-pyridyl)-1,8-naphthyridine-3-carboxylate (2.1 g, m.p. 185°-186° C.). This compound was heated at 90°-100° C. with 25 ml of 2N sodium hydroxide for 5 minutes. The reaction mixture was treated with decolorizing charcoal and filtered. The filtrate was adjusted to pH 6-7 with acetic acid and chilled. The resulting solid was collected by filtration and recrystallized from ethanol to give 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-pyridyl)-1,8-naphthyridine-3-carboxylic acid (Compound 1) (1.5 g, m.p. 286°-288° C.).

Workup

  1. temperaturewas heated at 50°-60° C. for 10 minutes
  2. temperatureheating
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated to dryness in vacuo
  5. additionthe residue was taken up in a mixture of chloroform and water
  6. customThe chloroform layer was separated
  7. customthe chloroform was evaporated in vacuo
  8. customto give crystals which
  9. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-598d646729bc48328c3f6a09614cdd1a
Source dataset
uspto-grants-1985_02
Patent number
US04497816

Reaction notes

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