N-bromobutanimide → HCID 16064396, compound

HRID 2425514Notes

Reaction equation

HRID 2425514 reaction equation
[CH3:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([NH:14][C@H:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:16][CH3:17])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.C1C(=O)N([Br:37])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:37][CH2:1][C:2]1[C:3]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([NH:14][C@H:15]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:16][CH3:17])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 66040093-Methyl-2-phenyl-N-(1-phenylpropyl)quinoline-4-carboximidic acid

Product 1

HCID 16064396HCID 16064396, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-methyl-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (9.8 g, 26 mmol) was dissolved in 200 mL hot CCl4 (with stirring) under N2 and heated at a gentle reflux. NBS (6.9 g, 39 mmol) was added and solution irradiated with long wave UV light for 0.5 h. Additional NBS (1.9 g, 11 mmol) was added and solution irradiated and refluxed for another 0.5 h. It was then allowed to cool and concentrated under reduced pressure to remove most of the CCl4. The residue was then dissolved in CH2Cl2 and washed with aqueous NaHCO3 containing a few crystals of sodium thiosulfate. The organic layer was then dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting material was then purified using silica gel chromatography (0-15% EtOAc/CH2Cl2) to give 2.9 g of desired product (24%) as a yellow-white solid. 1H NMR (300 MHz, CDCl3, 52° C.) δ 8.11 (d, J=8.1 Hz, 1H), 7.81-7.67 (m, 2H), 7.67-7.58 (m, 2H), 7.55-7.26 (m, 9H), 6.39 (d, J=7.8 Hz, 1H), 5.28 (q, J=7.6 Hz, 1H), 4.74-4.50 (m, 2H), 2.23-1.91 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); LCMS: m/z 459 (MH+).

Workup

  1. temperatureheated at a gentle reflux
  2. customsolution irradiated with long wave UV light for 0.5 h
  3. customsolution irradiated
  4. temperaturerefluxed for another 0.5 h
  5. temperatureto cool
  6. concentrationconcentrated under reduced pressure
  7. customto remove most of the CCl4
  8. dissolutionThe residue was then dissolved in CH2Cl2
  9. washwashed with aqueous NaHCO3 containing a few crystals of sodium thiosulfate
  10. dry with materialThe organic layer was then dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting material was then purified

Sources & evidence

ORD record
ord-0ff7fd02034c4d92aa67147e691bd84d
Source dataset
uspto-grants-2011_06
Patent number
US07964733B2

Reaction notes

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