Ammonium Acetate → HCID 19373031, compound

HRID 128937Notes

Reaction equation

HRID 128937 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[C:11](=[O:18])CO2)[CH:5]=[CH:6][CH:7]=1.[C:19]([O-])(=O)C.[NH4+:23]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[NH:23][CH:19]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 53705077HCID 53705077, compound

Product 1

HCID 19373031HCID 19373031, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-(3-chlorophenyl)pyrano [3,4-b]pyridin-5-one (1.25 g., 4.9 mmoles) in 20 ml DMF was added solid ammonium acetate (0.56 g., 7.29 mmoles). The reaction was heated at 50° C. under nitrogen for one hour, cooled and concentrated under vacuum. The solid was triturated with ether to give 1.1 grams (88% yield) 8-(3-chlorophenyl)-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 252°-252.5° C.; 1H NMR (DMSO-d6, 300 MHz) δ7.37-7.66 (m, 6H), 8.58 (dd, 1H, J=8.2, 2.1), 8.94 (dd, 1H, J=4.69, 1.68), 11.85 (bs, 1H); 13C NMR (75 MHz, DMSO-d6) δ161.74, 154.04, 151.91, 137.69, 135.62, 132.47, 132.26, 129.68, 129.55, 128.43, 126.64, 121.85, 121.60, 116.87; IR (KBr) vmax 3437, 3173, 3032, 2951, 2878, 1672, 1630, 1593, 1566, 1477, 1462, 1417, 1340, 1236, 821, 794, 692, 671, 603, 555 cm-1 ; mass spectrum (EI), m/e 256. Anal. (C14H9ClN2O) Calcd.: C, 65.51; H, 3.53; N, 10.91; C1, 13.81. Found: C, 65.67; H, 3.34; N, 10.98; C1, 13.91.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under vacuum
  3. customThe solid was triturated with ether

Sources & evidence

ORD record
ord-d7741d15c2084328923cf7f9f1f6be93
Source dataset
uspto-grants-1995_11
Patent number
US05466697

Reaction notes

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