Triethylamine → HCID 831395, compound

HRID 515204Notes

Reaction equation

HRID 515204 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH2:11])[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>ClCCl>[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:11][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 113598-AminoquinolineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 831395HCID 831395, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of compound quinolin-8-yl-amine (3.0 g, 20.8 mmol) in dichloromethane (40 ml) and triethylamine (3.1 ml, 21.9 mmol), 4-bromo-benzoyl chloride (4.8 g, 21.9 mmol) in dichloromethane (20 ml) is added drop wise at room temperature and the resulting mixture is stirred for 16 h. After completion of the reaction (monitored by TLC) the mixture is diluted with dichloromethane (100 ml) and washed with water and saturated sodium hydrogen carbonate solution. The organic layer is dried over sodium sulfate and concentrated in vacuo. The resulting crude product is purified by column chromatography (silica gel, 10% ethyl acetate/hexane) to obtain 4-bromo-N-quinolin-8-yl-benzamide (5.2 g, 15.9 mmol, 76%).

Workup

  1. customAfter completion of the reaction (monitored by TLC) the mixture
  2. washwashed with water and saturated sodium hydrogen carbonate solution
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude product is purified by column chromatography (silica gel, 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7adfc7c157e04dd49d5fba20a19fbd98
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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