Allyl bromide → HCID 12770911, compound

HRID 434566Notes

Reaction equation

HRID 434566 reaction equation
Cl.[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:12]=2[F:14])[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]1)[CH3:3].C(N(CC)CC)C.[CH2:33](Br)[CH:34]=[CH2:35]>CN(C=O)C>[CH2:35]([N:18]1[CH2:17][CH2:16][N:15]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5][N:4]3[CH2:2][CH3:3])=[CH:9][C:10]=2[F:21])[CH2:20][CH2:19]1)[CH:34]=[CH2:33]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 12770893HCID 12770893, compound

Product 1

HCID 12770911HCID 12770911, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3carboxylic acid hydrochloride (0.18 g), triethylamine (0.12 g), allyl bromide (0.09 g), and DMF (3 ml) was heated with stirring at 90° for 3 hours and the solvent was evaporated. The residue was dissolved in 2N sodium hydroxide solution. The alkaline solution was adjusted to pH 7 with aqueous acetic acid and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated. The residue was recrystallized from a mixture of DMF and ethanol to give 7-(4-allyl-1-piperazinyl)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.055 g), mp 227°-230° C. (decomp.).

Workup

  1. temperaturewas heated
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in 2N sodium hydroxide solution
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customThe residue was recrystallized from a mixture of DMF and ethanol

Sources & evidence

ORD record
ord-df06e0da7e5a4fd19395ad74c2b33431
Source dataset
uspto-grants-1983_08
Patent number
US04398029

Reaction notes

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