N-bromobutanimide → HCID 10321326, compound

HRID 1987024Notes

Reaction equation

HRID 1987024 reaction equation
[Br:1][C:2]1[CH: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])[N:3]=1.C1C(=O)N(Br)C(=O)C1.C1CCN2C(=NCCC2)CC1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:1][C:2]1[CH: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])[N:3]=1

Participants

7

Reactant 4

HCID 67184N-bromobutanimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 10253075HCID 10253075, compound

Product 1

HCID 10321326HCID 10321326, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

7-Bromo-1,5-bis(2-chlorophenyl)-3,4-dihydro[1,6]naphthyridin-2(1H)-one (30 mg, 0.067 mmol) in carbon tetrachloride (5 ml) was treated with NBS (15 mg) and AlBN (1.1 mg) and heated under reflux for 1.5 h. DBU (10 μl) was added, the mixture cooled, and dichloromethane (5 ml) added, followed by 8% sodium bicarbonate (10 ml). The mixture was passed through a hydrophobic frit and evaporated in vacuo to give the product as an off-white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 h
  3. temperaturethe mixture cooled
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-1fa692eb4ee343f3a2ae2e262cc03c70
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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