Potassium Carbonate → 7-chloro-3-(3,5-dimethoxyphenyl)-1,8-dimethyl-1,6-naphthyridin-2(1H)-one

HRID 524067

Reaction equation

HRID 524067 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([NH:11][CH3:12])[C:5]([CH:6]=O)=[CH:4][N:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][C:24](OC)=[O:25])[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]2[C:5]([CH:6]=[C:23]([C:17]3[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=[C:15]([O:14][CH3:13])[CH:16]=3)[C:24](=[O:25])[N:11]2[CH3:12])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 592191Methyl 3,5-dimethoxyphenylacetateHCID 867135906-Chloro-5-methyl-4-(methylamino)nicotinaldehyde

Product 1

HCID 867135917-chloro-3-(3,5-dimethoxyphenyl)-1,8-dimethyl-1,6-naphthyridin-2(1H)-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 6-chloro-5-methyl-4-(methylamino)nicotinaldehyde (3.11 g, 16.8 mmol), methyl 2-(3,5-dimethoxyphenyl)acetate (4.25 g, 20.2 mmol) and potassium carbonate (2.8 g, 20.3 mmol) in N,N-dimethylformamide (100 mL) was stirred at 105° C. overnight. LCMS monitored the reaction was completed. The reaction mixture was cooled to RT and quenched by water. The precipitate was filtered and dried to get the title compound (5.5 g, crude) as a yellow solid. MS (ES+) C18H17ClN2O3 requires: 344, 346. found: 345, 347 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customquenched by water
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-b5d4d1ac9f7148c394290c2b063189d3
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Linked notes

Loading…