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

HRID 2274196Notes

Reaction equation

HRID 2274196 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([NH:10][CH3:11])[C:5]([CH:6]=O)=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH2:22][C:23](OC)=[O:24])[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]2[C:5]([CH:6]=[C:22]([C:16]3[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=[C:14]([O:13][CH3:12])[CH:15]=3)[C:23](=[O:24])[N:10]2[CH3:11])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 592191Methyl 3,5-dimethoxyphenylacetateHCID 234345716-Chloro-4-(methylamino)nicotinaldehyde

Product 1

HCID 867135767-chloro-3-(3,5-dimethoxyphenyl)-1-methyl-1,6-naphthyridin-2(1H)-oneYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 6-chloro-4-(methylamino)nicotinaldehyde (3.7 g, 21.7 mmol), methyl 2-(3,5-dimethoxyphenyl)acetate (4.5 g, 21.7 mmol) and potassium carbonate (9.0 g, 65.1 mmol) in N,N-dimethylformamide (30 mL) was heated at 105° C. for 5 h. LCMS showed the reaction was completed. The reaction was cooled to RT, quenched with water (200 mL), and filtered. The filtration cake was washed by petroleum ether (50 mL) and ethyl acetate (50 mL) to afford the title compound (5.8 g, 77%) as a yellow solid. MS (ES+) C18H19ClN2O3 requires: 346, 348. Found: 347, 349 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to RT
  2. customquenched with water (200 mL)
  3. filtrationfiltered
  4. washThe filtration cake was washed by petroleum ether (50 mL) and ethyl acetate (50 mL)

Sources & evidence

ORD record
ord-aa4daaab84e0467a98b543073ec60f0d
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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