Heptanoyl chloride → N-[(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]heptanamide

HRID 384490

Reaction equation

HRID 384490 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:16])[C:14]=1[CH3:15])=[CH:11][CH:10]=[CH:9][CH:8]=2.[C:17](Cl)(=[O:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>N1C=CC=CC=1>[CH3:15][C:14]1[C:13](=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH2:4][NH:3][C:17](=[O:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 17313Heptanoyl chlorideHCID 685107592-(aminomethyl)-3-methylquinolin-4(1H)-one dihydrochloride

Product 1

HCID 59527359N-[(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]heptanamideYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice-cold solution of 2-(aminomethyl)-3-methylquinolin-4(1H)-one dihydrochloride (160 mg) in pyridine (5 mL) was added heptanoic acid chloride (110 mg), and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was concentrated under reduced pressure, and then water (40 mL) was added to the residue. The resulting solid was collected by filtration, washed with water, and dried. This solid was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain N-[(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]heptanamide (127 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionwater (40 mL) was added to the residue
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customdried
  6. customThis solid was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-1574a40806bd4a6ea1064a7cd9ea61b0
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Linked notes

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