Water → 4-Oxo-1,4-dihydroquinoline-3-carboxamide

HRID 2227159

Reaction equation

HRID 2227159 reaction equation
OCC1C=CC(C[NH:8][C:9]([C:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[O:10])=CC=1.S(Cl)(Cl)=O.O>CN(C=O)C.[Cl-].[Na+].O>[O:21]=[C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=[C:11]1[C:9]([NH2:8])=[O:10]

Participants

6

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 12051693N-[4-(hydroxymethyl)benzyl] 4-oxo-1,4-dihydro-quinoline-3-carboxamide

Product 1

HCID 8246704-Oxo-1,4-dihydroquinoline-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of N-[4-(hydroxymethyl)benzyl] 4-oxo-1,4-dihydro-quinoline-3-carboxamide (279 mg; 0.79 mmol) in anhydrous DMF (8 mL) at 0° is added thionyl chloride (61 μL; 0.83 mmol) and the solution is stirred at room temperature for 1 h. Water (10 mL) and brine (10 mL) are added, and the precipitate is collected, rinsed with a small quantity of methanol and ether, and dried to give 214 mg of N-[4-chloromethyl)benzyl] 4-oxo-1,4-dihydro-quinoline-3-carboxamide.

Workup

  1. customthe precipitate is collected
  2. washrinsed with a small quantity of methanol and ether
  3. customdried

Sources & evidence

ORD record
ord-b72fbba407cd4ed9aff6fecaeccbc553
Source dataset
uspto-grants-2002_07
Patent number
US06413956B1

Linked notes

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