Water → Ethyl 6-Chloro-1-methyl-4-oxo-1,4-dihydro[1,5]naphthyridine-3-carboxylate

HRID 1070656Notes

Reaction equation

HRID 1070656 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:5]2[OH:17].[C:18](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:18])[CH:7]=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]2=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469542Ethyl 6-chloro-4-hydroxy[1,5]naphthyridine-3-carboxylate

Product 1

HCID 22397136Ethyl 6-Chloro-1-methyl-4-oxo-1,4-dihydro[1,5]naphthyridine-3-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 6-chloro-4-hydroxy[1,5]naphthyridine-3-carboxylate (Preparation 58, 694 mg), potassium carbonate (588 mg), and iodomethane (264 μL) in DMF (15 mL) is stirred at room temperature for 5 hours. The mixture is poured into water (50 mL), and the solution is extracted with CH2Cl2 (3×50 mL). The organic layers are dried (MgSO4) and concentrated. Trituration with ether (50 mL) affords 473 mg (65%) of the title compound as an off-white solid. Physical Characteristics. 1H NMR (DMSO-d6) δ8.70, 8.31, 7.90, 4.24, 3.92, 1.29; HRMS (FAB) m/z 267.0535 (C12H11ClN2O3+H). Anal. Found: C, 54.14; H, 4.24; N, 10.58.

Workup

  1. extractionthe solution is extracted with CH2Cl2 (3×50 mL)
  2. dry with materialThe organic layers are dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2f89db75b04f478a8ef350bb3765390a
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Reaction notes

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