Sodium hydride → HCID 20375643, compound

HRID 1390294Notes

Reaction equation

HRID 1390294 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([F:23])[CH:21]=2)[NH:16][C:15](=[O:24])[CH:14]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([Br:35])[C:33]=1[Br:34])[CH2:29]Br>CN(C)C=O.O>[CH2:3]([O:10][CH2:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([F:23])[CH:21]=2)[N:16]([CH2:29][C:28]2[CH:27]=[C:26]([Br:25])[C:33]([Br:34])=[C:32]([Br:35])[CH:31]=2)[C:15](=[O:24])[CH:14]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 203756274-[2-(Benzyloxy)ethyl]-6-fluoroquinolin-2(1H)-oneHCID 20375648HCID 20375648, compound

Product 1

HCID 20375643HCID 20375643, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of sodium hydride (0.675g. of 80% w/w suspension; freed of mineral oil as in Example 1) in dimethylformamide (100ml.) under a nitrogen atmosphere was added 4-(2-benzyloxyethyl)-6-fluoro-1,2-dihydro-2-oxoquinoline (6.0g.). The mixture was stirred at 40° C. for one hour and then treated at this temperature with 3,4,5-tribromobenzylbromide (9.1g.). The mixture was stirred overnight at ambient temperature and then diluted with water (200 ml.) and the product extracted with ethyl acetate (3 × 150ml.). The combined organic extracts were washed with water (2 × 100ml.), dried (MgSO4), and evaporated. The residue was a mixture of O- and N-substituted products. Chromatography of this residue on silica gel using a 50:50 v/v mixture of ether and petroleum ether (b.p. 40°-60° C.) as eluant gave 4-(2-benzyloxyethyl)-6-fluoro-1-(3,4,5-tribromobenzyl)-1,2-dihydro-2-oxoquinoline, as an oil, Infra-Red Spectral Absorption ν max. 1665 cm.-1.

Workup

  1. stirringThe mixture was stirred overnight at ambient temperature
  2. extractionthe product extracted with ethyl acetate (3 × 150ml.)
  3. washThe combined organic extracts were washed with water (2 × 100ml.)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. additiona mixture of O- and N-substituted products
  7. additionChromatography of this residue on silica gel using a 50:50 v/v mixture of ether and petroleum ether (b.p. 40°-60° C.) as eluant

Sources & evidence

ORD record
ord-8f285e50d4bb471dabadd271e1189797
Source dataset
uspto-grants-1979_02
Patent number
US04138490

Reaction notes

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