Water → HCID 178464440, compound

HRID 2389288Notes

Reaction equation

HRID 2389288 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=O)[CH:3]=1.[CH2:15]([NH:17][CH3:18])[CH3:16].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:15]([N:17]([CH3:18])[C:12]([C:4]1[CH:3]=[C:2]([OH:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)=[O:14])[CH3:16]

Participants

8

Reactant 6

HCID 962WaterHCID 12219N-MethylethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418933HCID 178418933, compound

Product 1

HCID 178464440HCID 178464440, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxyquinoline-2-carboxylic acid (1.00 g, 5.29 mmol) was dissolved in DMF (10 mL), and N-ethylmethylamine (91 μL, 10.6 mmol), WSC.HCl (2.03 g, 10.6 mmol), and HOBt.H2O (1.62 g, 10.6 mmol), were added thereto, and the mixture was stirred at room temperature for 3 hours. To the mixture, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=95/5) to give N-ethyl-4-hydroxy-N-methyl-quinoline-2-carboxamide (615 mg, 2.67 mmol, yield: 50%). Mass (m/e): 231 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-f9bacbb3dd234f0e96b2addfff72d126
Source dataset
uspto-grants-2012_09
Patent number
US08273738B2

Reaction notes

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