3-Bromoaniline → HCID 57516627, compound

HRID 1898575Notes

Reaction equation

HRID 1898575 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][C:10]1([CH3:17])[CH2:14][C:13](=O)[O:12][C:11]1=[O:16].C(N1C=CN=C1)(N1C=CN=C1)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:12])[CH2:14][C:10]([CH3:17])([CH3:9])[C:11]2=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 682631,1'-CarbonyldiimidazoleHCID 870672,2-Dimethylsuccinic anhydride

Product 1

HCID 57516627HCID 57516627, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

3-Bromophenylamine (10.0 g, 58.1 mmol) and 3,3-dimethyl-dihydro-furan-2,5-dione (8.2 g, 63.9 mmol) were suspended in 300 ml DCM. The reaction was stirred at 50° C. for 3 h. The reaction was cooled to room temperature and 1,1′-carbonyldiimidazole (11.3 g, 69.7 mmol) was added in portions. The reaction was heated again to 50° C. and stirred overnight. The solvent was evaporated and the product was crystallized from isopropyl alcohol to give 9.3 g of 1-(3-bromophenyl)-3,3-dimethyl-pyrrolidine-2,5-dione. The mother liquor was concentrated and chromatographed using a gradient of 0% to 20% ethyl acetate in hexanes to give another 1.3 g of product for a combined yield of 10.6 g (65%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. temperatureThe reaction was heated again to 50° C.
  3. stirringstirred overnight
  4. customThe solvent was evaporated
  5. customthe product was crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-93bf0a0a40b0407d9ee735cd9ebcf23f
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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