Allyl bromide → HCID 22105593, compound

HRID 1455956Notes

Reaction equation

HRID 1455956 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:10]=1[CH2:11][NH:12][C:13]1[NH:18][C:17](=[O:19])[C:16]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:36](Br)[CH:37]=[CH2:38].[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:10]=1[CH2:11][NH:12][C:13]1[N:18]=[C:17]([O:19][CH2:38][CH:37]=[CH2:36])[C:16]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 22105683HCID 22105683, compound

Product 1

HCID 22105593HCID 22105593, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 6-[2-benzyloxy-5-bromobenzylamino]-2-oxo-1,2-dihydropyridine-3-carboxylate (2.78 g), sodium carbonate (0.97 g) and allyl bromide (0.77 ml) in DMF (10 ml) was stirred for 5 days, poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic solution was washed with HCl solution, saturated aqueous sodium hydrogen carbonate and brine, dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography, eluting with 2.5% ethyl acetate/dichloromethane, to give ethyl 6-[2-benzyloxy-5-bromobenzylamino]-2-allyloxypyridine-3-carboxylate (1.99 g) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic solution was washed with HCl solution, saturated aqueous sodium hydrogen carbonate and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography
  7. washeluting with 2.5% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-1190898aa0854fcd94fc638107d6c8fe
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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