Hydrochloric Acid → 5-Bromo-pyridine-2-carboxylic acid (4-chloro-phenyl)-amide

HRID 1024190

Reaction equation

HRID 1024190 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](Cl)=[O:9])=[N:6][CH:7]=1.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.N1C=CC=CC=1.Cl>C(#N)C.CN(C)C1C=CN=CC=1.O>[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[O:9])=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 78124-ChloroanilineHCID 190907715-Bromo-pyridine-2-carbonyl chloride

Product 1

HCID 595933715-Bromo-pyridine-2-carboxylic acid (4-chloro-phenyl)-amide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
68 °C

Procedure

To 5-Bromo-pyridine-2-carbonyl chloride (69, 0.76 g, 3.4 mmol) in acetonitrile (29.0 mL) were added p-chloroaniline (53, 0.702 g, 5.50 mmol), 4-dimethylamino-pyridine (0.12 g, 0.96 mmol) and pyridine (2.9 mL, 0.036 mol). The reaction was stirred at 68° C. overnight, then poured into water, acidified with 1N HCl to pH around 1 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with dichloromethane to give a white solid (70, 0.75 g, 70.0%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with dichloromethane
  7. customto give a white solid (70, 0.75 g, 70.0%)

Sources & evidence

ORD record
ord-8d55364b25e644b4a76c53b27d8e02a8
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Linked notes

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