Allyl bromide → Allyl 5-amino-2-nitrobenzoate

HRID 1736376Notes

Reaction equation

HRID 1736376 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22]>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([O:9][CH2:22][CH:21]=[CH2:20])=[O:8]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 832985-Amino-2-nitrobenzoic acid

Product 1

HCID 19432493Allyl 5-amino-2-nitrobenzoateYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Amino-2-nitrobenzoic acid (4 g, 22 mM) was dissolved in DMF (40 ml) and anhydrous potassium carbonate (3.64 g, 26.4 mM) added while stirring. Allyl bromide (3.86 g, 26.4 mM) was added and the mixture stirred at ambient temperature overnight. The solvent was removed by evaporation and the residue taken up in acetonitrile. The organic layer was washed with water, dried (MgSO4) evaporated and purified by silica chromatography with acetonitrile/petroleum ether (40/60) to give allyl 5-amino-2-nitrobenzoate as a yellow solid (3.46 g, 71%).

Workup

  1. stirringthe mixture stirred at ambient temperature overnight
  2. customThe solvent was removed by evaporation
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. custompurified by silica chromatography with acetonitrile/petroleum ether (40/60)

Sources & evidence

ORD record
ord-ca4ed12172924dbe84e81d18112ea7d2
Source dataset
uspto-grants-1996_07
Patent number
US05541178

Reaction notes

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