N-bromobutanimide → HCID 57723000, compound

HRID 1987038Notes

Reaction equation

HRID 1987038 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:19])[N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[CH:3]=1.C1C(=O)N(Br)C(=O)C1.C1CCN2C(=NCCC2)CC1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:19])[N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[CH:3]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimide2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86607812HCID 86607812, compound

Product 1

HCID 57723000HCID 57723000, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

7-Chloro-1,5-bis(2-chlorophenyl)-3,4-dihydro[1,8]naphthyridin-2(1H)-one (220 mg, 0.545 mmol) in carbon tetrachloride (3 ml) was treated with NBS (110 mg; 0.618 mmol) and AlBN (1 mg) and heated under reflux for 1 h. Further NBS (110 mg, 0.618 mmol) and AlBN (2 mg) were added and heating under reflux continued for a further 2 h. DBU (0.2 ml) was added, the mixture cooled, filtered, and further carbon tetrachloride (3 ml) added, followed by 2M hydrochloric acid (3 ml). The mixture was purified by column chromatography over silica (20 g) eluting with cyclohexane-ethyl acetate (100:0-60:40) to afford the title compound as a white solid (151 mg, 69%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. temperatureheating
  4. temperatureunder reflux
  5. temperaturethe mixture cooled
  6. filtrationfiltered
  7. additionfurther carbon tetrachloride (3 ml) added
  8. customThe mixture was purified by column chromatography over silica (20 g)
  9. washeluting with cyclohexane-ethyl acetate (100:0-60:40)

Sources & evidence

ORD record
ord-d9919683c64f46d4a86651a9b3cbced9
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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