Iodoethane → HCID 13477662, compound

HRID 370713Notes

Reaction equation

HRID 370713 reaction equation
Cl.[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:14]3[CH2:19][CH2:18][NH:17][CH:16]([CH3:20])[CH2:15]3)[CH:12]=2)[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]1)[CH3:3].[CH2:26](I)[CH3:27].C(N(CC)CC)C>CN(C)C=O>[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:14]3[CH2:19][CH2:18][N:17]([CH2:26][CH3:27])[CH:16]([CH3:20])[CH2:15]3)[CH:12]=2)[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]1)[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 30624361-Ethyl-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid--hydrogen chloride (1/1)

Product 1

HCID 13477662HCID 13477662, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.00 g of 1-ethyl-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid hydrochloride, 1.29 g of ethyl iodide and 1.09 g of triethylamine in 20 ml of N,N-dimethylformamide was heated at 70° to 80° C. for 1.5 hours. The solvent of the reaction mixture was evaporated and the residue was acidified with 50% aqueous acetic acid. The solution was neutralized with 20% aqueous sodium hydroxide and the precipitate was filtered. The precipitate was chromatographed on silica gel using chloroform-methanol (9:1) as eluent to give 0.47 g of the title compound as colorless crystalls, which was recrystallized from a mixture of chloroform and methanol as colorless needles, M.p. 203°-205° C.

Workup

  1. customThe solvent of the reaction mixture was evaporated
  2. filtrationthe precipitate was filtered
  3. customThe precipitate was chromatographed on silica gel

Sources & evidence

ORD record
ord-a92f15e714c14af3b947ab4eb76e57cd
Source dataset
uspto-grants-1985_07
Patent number
US04528287

Reaction notes

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