3-Bromoaniline → HCID 86083506, compound

HRID 2367131Notes

Reaction equation

HRID 2367131 reaction equation
C([CH2:3][C:4](=O)[CH2:5][CH:6](Cl)[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([N+:16]([O-:18])=[O:17])[CH:8]=1)C.[Br:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25].CN(C)C(=[O:33])C>>[Br:21][C:22]1[CH:23]=[C:24]([N:25]2[CH:6]([C:7]3[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([N+:16]([O-:18])=[O:17])[CH:8]=3)[CH2:5][CH2:4][C:3]2=[O:33])[CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 115623-BromoanilineHCID 31374DimethylacetamideHCID 86617517HCID 86617517, compound

Product 1

HCID 86083506HCID 86083506, compoundYield 28%

Conditions

Temperature
120 °C

Procedure

Ethyl 4-chloro-4-(3,4-dinitrophenyl)butanone (366.3 mg, 1.2 mmol.), 3-bromoaniline (220 mg, 1.3 mmol.) and N,N-dimethylacetamide (0.3 mL) were combined and heated to 120° C. over 17 hours under a nitrogen atmosphere. The mixture was then cooled to room temperature and partitioned with ethyl acetate and water. The organic layer was washed twice with additional water, then brine and dried over anhydrous sodium sulfate. Filtration and concentration followed by purification of the residue by silica gel flash chromatography (100% ethyl acetate eluent) gave 1-(3-bromophenyl)-5-(3,4-dinitrophenyl)pyrrolidin-2-one (132 mg, 28% yield) as an amorphous residue. The material thus obtained is contaminated by variable amounts of 5-(3,4-dinitrophenyl)dihydrofuran-2(3H)-one as a side product and is carried forward without further purification. MS (EI) for C16H12N3O5Br: 407 (MH+).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. custompartitioned with ethyl acetate and water
  3. washThe organic layer was washed twice with additional water
  4. dry with materialbrine and dried over anhydrous sodium sulfate
  5. filtrationFiltration and concentration
  6. customfollowed by purification of the residue by silica gel flash chromatography (100% ethyl acetate eluent)

Sources & evidence

ORD record
ord-c8effdf162fa4e4bb40ac58388eb5e81
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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