Iodoethane → HCID 70454196, compound

HRID 1284504Notes

Reaction equation

HRID 1284504 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH:16]([CH3:20])[CH2:15]4)[CH:12]=3)[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:26]([I:28])[CH3:27].C(N(CC)CC)C>CN(C)C=O>[OH2:22].[IH:28].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH2:26][CH3:27])[CH:16]([CH3:20])[CH2:15]4)[CH:12]=3)[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 1852361-Cyclopropyl-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 70454196HCID 70454196, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.7 g (0.005 mol) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-methyl-1-piperazinyl)-3-quinolinecarboxylic acid, 1.7 g (0.011 mol) of ethyl iodide and 1.1 g of triethylamine in 20 ml of dimethylformamide is heated at 80° C. for 3 hours. The solution is concentrated in vacuo, the crystalline residue is stirred with 10 ml of water and the undissolved product is recrystallized from methanol. 0.6 g (32% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-ethyl-3-methyl-1-piperazinyl)-3-quinolinecarboxylic acid hydriodide monohydrate of decomposition point 285°-288° C. is obtained.

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. customthe undissolved product is recrystallized from methanol

Sources & evidence

ORD record
ord-6b1ca25482d343db8401e15caa50d629
Source dataset
uspto-grants-1986_01
Patent number
US04563459

Reaction notes

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