Ammonium Acetate → HCID 15293173, compound

HRID 128936Notes

Reaction equation

HRID 128936 reaction equation
[C:1]1([CH:7]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10](=[O:17])CO2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O-])(=O)C.[NH4+:22]>CN(C=O)C>[C:1]1([C:7]2[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[NH:22][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 54500696HCID 54500696, compound

Product 1

HCID 15293173HCID 15293173, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-phenylpyrano[3,4-b]pyridin-5-one (340 mg, 1.5 moles) in 10 ml DMF was added solid ammonium acetate (180 mg, 2.3 mmoles). The solution was heated to 80° C. under nitrogen for 18 hours, cooled and concentrated under vacuum. The solution was then flashed chromatographed eluting with ethyl acetate to give 245 mg (73% yield) of the desired 8-phenyl-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 260°-263° C.; 1H NMR (DMSO-d6, 300 MHz) δ7.38-7.65 (m, 7H), 8.64 (dd, 1H, J=8.1, 1.8 Hz), 8.98 (dd, 1H, J=4.5, 2.0 Hz), 11.83 (b, 1H); 13C NMR (75 MHz, DMSO-d6) δ 161.72, 153.98, 152.24, 135.55, 131.56, 129.93, 127.79, 126.77, 121. 62, 118.43; mass spectrum (EI), m/e 222.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under vacuum
  3. customThe solution was then flashed chromatographed
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d2cf73834d2843fd9fd33f5510fc2834
Source dataset
uspto-grants-1995_11
Patent number
US05466697

Reaction notes

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