Hydrogen Bromide → HCID 10935033, compound

HRID 724829Notes

Reaction equation

HRID 724829 reaction equation
[C:1]([OH:11])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br.[N+:13]([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)([O-:15])=[O:14]>CC(=O)CC>[N+:13]([C:16]1[CH:22]=[CH:21][C:19]([NH:20][CH:3]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:2][C:1]([OH:11])=[O:10])=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 74754-NitroanilineHCID 444539Cinnamic Acid

Product 1

HCID 10935033HCID 10935033, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of trans-cinnamic acid (2 g, 13 mmol) and HBr (30% solution in AcOH, 40 mL) was stirred at room temperature for 18 h and then evaporated to dryness. The resulting solid was taken upin 2-butanone (100 mL) and p-nitroaniline (5 g, 36 mmol) was added. The reaction mixture was refluxed for 18 h, allowed to cool and partitioned between CHCl3 and 1N HCl. The organic phase was dried and concentrated to a residue. This was purified by chromatography on silica gel (hexane: EtOAc, 50%), to afford the title compound as a yellow solid (0.78 g, 21%).

Workup

  1. customevaporated to dryness
  2. additionwas added
  3. temperatureThe reaction mixture was refluxed for 18 h
  4. temperatureto cool
  5. custompartitioned between CHCl3 and 1N HCl
  6. customThe organic phase was dried
  7. concentrationconcentrated to a residue
  8. customThis was purified by chromatography on silica gel (hexane: EtOAc, 50%)

Sources & evidence

ORD record
ord-f06f38a60a044183b5729701f27a32cf
Source dataset
uspto-grants-1998_01
Patent number
US05705504

Reaction notes

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