Pyridine → Quinoline carboxamide derivative 1

HRID 1259845

Reaction equation

HRID 1259845 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([C:17](Cl)=[O:18])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[NH2:26][C:27]1[O:28][C:29]([C:32]2[O:33][CH:34]=[CH:35][CH:36]=2)=[N:30][N:31]=1>CO>[O:33]1[CH:34]=[CH:35][CH:36]=[C:32]1[C:29]1[O:28][C:27]([NH:26][C:17]([C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:16]=2)=[O:18])=[N:31][N:30]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2021855-(Furan-2-yl)-1,3,4-oxadiazol-2-amineHCID 27604092-Phenylquinoline-4-carbonyl chloride

Product 1

HCID 4253236Quinoline carboxamide derivative 1Yield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

2-phenyl-4-quinolinecarbonyl chloride (2.00 g, 7.47 mmol) was added in small portions to a pyridine (40 mL) solution of commercially available 2-amino-5-(2-furyl)-1,3,4-oxadiazole (1.69 g, 11.2 mmol), and the mixture was heated with stirring at 60° C. for 6 hours. To the reaction solution, methanol was added, and the solvent was distilled off. The obtained residue was triturated by the addition of water. The deposited crystal was collected by filtration, washed with methanol and then with ethyl acetate, and then recrystallized from DMF-methanol to obtain the title compound (1.23 g, 3.22 mmol) as a light brown powder (yield: 43%).

Workup

  1. temperaturethe mixture was heated
  2. distillationthe solvent was distilled off
  3. customThe obtained residue was triturated by the addition of water
  4. filtrationThe deposited crystal was collected by filtration
  5. washwashed with methanol
  6. customwith ethyl acetate, and then recrystallized from DMF-methanol

Sources & evidence

ORD record
ord-ee5b437691344d60bdb8eed564e0619d
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Linked notes

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