Dimethylformamide → HCID 57584187, compound

HRID 910620Notes

Reaction equation

HRID 910620 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[C:6]1=[O:20].C[N:23]([CH3:26])C=O.[C:27](Cl)(=[O:31])[C:28](Cl)=O>ClC(Cl)C>[NH2:5][C:6]1[CH:7]=[CH:8][CH:28]=[C:27]([OH:31])[C:26]=1[NH:23][C:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([C:7]2[C:6](=[O:20])[N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:21])[CH:10]=[CH:9][CH:8]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 57583919HCID 57583919, compound

Product 1

HCID 57584187HCID 57584187, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4-{1-[2-(Dimethylamino)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoic acid (1.46 g) was suspended in dichloroethane (15 ml), dimethylformamide (125 μL) was added, and oxalyl chloride (367 μL) was dropwise added dropwisely at room temperature. After stirring at room temperature for 30 minutes, the reaction mixture was evaporated under reduced pressure. A dichloromethane (10 ml)-pyridine (10 ml) solution of 2-amino-3-nitrophenol (499 mg) was added to the resulting residue, followed by stirring overnight at room temperature. The reaction suspension was filtered, and the filtrate was evaporated under reduced pressure. The substance collected by filtration and the filtration residue were dissolved in a mixed solvent of ethanol (14.6 mL)-water (14.6 mL), and an aqueous 1 M hydrochloric acid solution (3.24 mL) and iron (904 mg) were added, followed by heating under reflux for 3 hours. An aqueous saturated sodium hydrogencarbonate solution and chloroform were added to the reaction suspension, followed by vigorous stirring and filtration through Celite. The filtrate was extracted with chloroform, the organic layer was evaporated under reduced pressure, and the residue was purified by NH-silica gel column chromatography (chloroform:methanol=100:0 to 95:5) to obtain N-(2-amino-6-hydroxyphenyl)-4-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzamide (600 mg) as a brown solid.

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. additionA dichloromethane (10 ml)-pyridine (10 ml) solution of 2-amino-3-nitrophenol (499 mg) was added to the resulting residue
  3. stirringby stirring overnight at room temperature
  4. filtrationThe reaction suspension was filtered
  5. customthe filtrate was evaporated under reduced pressure
  6. filtrationThe substance collected by filtration
  7. dissolutionthe filtration residue were dissolved in a mixed solvent of ethanol (14.6 mL)-water (14.6 mL)
  8. additionan aqueous 1 M hydrochloric acid solution (3.24 mL) and iron (904 mg) were added
  9. temperatureby heating
  10. temperatureunder reflux for 3 hours
  11. additionAn aqueous saturated sodium hydrogencarbonate solution and chloroform were added to the reaction suspension
  12. stirringby vigorous stirring
  13. filtrationfiltration through Celite
  14. extractionThe filtrate was extracted with chloroform
  15. customthe organic layer was evaporated under reduced pressure
  16. customthe residue was purified by NH-silica gel column chromatography (chloroform:methanol=100:0 to 95:5)

Sources & evidence

ORD record
ord-7a5792a6030a46a3b66a596b42cbfc89
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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