Benzyl Bromide → Methyl 1-benzyl-5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate

HRID 598155Notes

Reaction equation

HRID 598155 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:16])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[N:6][NH:7]2.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+]>CN(C)C=O>[CH2:17]([N:7]1[C:8]2[C:3](=[C:2]([Cl:1])[CH:11]=[CH:10][CH:9]=2)[C:4](=[O:16])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[N:6]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 67267740Methyl 5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate

Product 1

HCID 67266995Methyl 1-benzyl-5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylateYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.00 g (4.2 mmol) of methyl 5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate and 0.86 g (5.0 mmol) of benzyl bromide in 30 mL of dimethylformamide was added 0.20 g (5.0 mmol) of sodium hydride (60% dispersion in mineral oil). The mixture was stirred for 4 h at room temperature and quenched with water. The mixture was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated onto silica gel. The crude material was purified by flash chromatography eluting with a 33-50% ethyl acetate/hexanes gradient mixture to give 0.86 g (62%) of the title compound as a light yellow solid.

Workup

  1. customquenched with water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated onto silica gel
  7. customThe crude material was purified by flash chromatography
  8. washeluting with a 33-50% ethyl acetate/hexanes gradient mixture

Sources & evidence

ORD record
ord-1525a56fbebb42908cffa07d39781943
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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