Water → 1-(4-Amino-3-nitrophenyl)-2-bromopropan-1-one

HRID 1517193Notes

Reaction equation

HRID 1517193 reaction equation
[Br:1][CH:2]([CH3:18])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11]C(=O)C)=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1)=[O:4].O>Br>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH:2]([Br:1])[CH3:18])=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 962WaterHCID 59569023HCID 59569023, compound

Product 1

HCID 595690141-(4-Amino-3-nitrophenyl)-2-bromopropan-1-oneYield 353.6%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
120 °C

Procedure

11.65 g (37 mM) of N-[4-(2-bromopropanoyl)-2-nitrophenyl]acetamide dissolved in aqueous 47% hydrobromic acid solution are maintained at 120° C. for 15 minutes with stirring. The reaction medium is then poured into water and extracted with ethyl acetate. The organic phase is washed with water, with aqueous sodium hydrogen carbonate solution and finally with saturated aqueous sodium chloride solution. The organic phase is separated out by settling, dried over anhydrous sodium sulfate and then evaporated under vacuum to give 35.7 g of 1-(4-amino-3-nitrophenyl)-2-bromopropan-1-one in the form of a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water, with aqueous sodium hydrogen carbonate solution and finally with saturated aqueous sodium chloride solution
  3. customThe organic phase is separated out
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-22bec6d5db21480b81aa8e435adf640d
Source dataset
uspto-grants-2012_07
Patent number
US08232272B2

Reaction notes

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