N-bromobutanimide → HCID 66876970, compound

HRID 2194953Notes

Reaction equation

HRID 2194953 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:4]([CH3:14])[CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:7]([Br:15])=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:4]([CH3:14])[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 54187007Methyl 3-(4-amino-2-methylphenyl)propanoate

Product 1

HCID 66876970HCID 66876970, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Intermediate 8 (1.4 g) in acetonitrile (20 ml) was added with N-bromosuccinimide (1.4 g, WAKO) under ice cooling, stirred for 10 minutes under ice cooling, and then stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, then added with ethyl acetate (10 ml), and successively washed with saturated aqueous ammonium chloride, 5% aqueous sodium sulfite, saturated aqueous sodium hydrogencarbonate and saturated brine, the organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1) to obtain the title compound (1.0 g).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionadded with ethyl acetate (10 ml)
  4. washsuccessively washed with saturated aqueous ammonium chloride, 5% aqueous sodium sulfite, saturated aqueous sodium hydrogencarbonate and saturated brine
  5. customthe organic layer was dried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-094f7a20e4f64cdd8b665e4ef526c289
Source dataset
uspto-grants-2012_12
Patent number
US08334314B2

Reaction notes

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