Hydrochloric Acid → HCID 19373036, compound

HRID 128943Notes

Reaction equation

HRID 128943 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11](=[O:18])[NH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[N:25]1[CH:30]=[CH:29][C:28]([CH2:31]Cl)=[CH:27][CH:26]=1.Cl>CN(C=O)C.O>[N:25]1[CH:30]=[CH:29][C:28]([CH2:31][N:10]2[CH:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]2=[O:18])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 745714-(Chloromethyl)pyridineHCID 19373031HCID 19373031, compound

Product 1

HCID 19373036HCID 19373036, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 8-(3-chlorophenyl)-1,6-naphthyridin-5-one (128 mg, 0.5 mmoles) and potassium carbonate (346 mg, 2.5 mmoles) in 20 ml DMF was added solid 4-picolyl chloride.HCl (164 mg, 1.0 mmole) under an atmosphere of nitrogen and stirred overnight at 21° C. The reaction mixture was poured into 100 ml water and after stirring for one hour the white precipitate was collected and dried. Crystallization from methanol gave 84 mg (48% yield) of the desired 6-(4-pyridylmethyl)-8-(3-chlorophenyl)-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 170.5°-172.5° C.; TLC in 1:1 EtOAc/Hex; 1H NMR (CDCl3, 300 MHz) δ5.20 (s, 2H), 7.15 (dd, 2H, J=4.7, 1.5), 7.28-7.50 (m, 6H), 8.52 (dd, 2H, J=4.4, 1.5), 8.69 (dd, 1H, J=8.1, 2.1), 8.90 (dd, 1H, J=4.7, 1.8); 13C NMR (75 MHz, CDCl3) δ161.86, 154.58, 151.75, 150.46, 144.94, 136.83, 136.59, 134.20, 134.01, 130.01, 129.58, 128.23, 127.98, 122.37, 122.32, 121.93, 120.47, 51.25; IR (KBr) vmax 3435, 3051, 1668, 1630, 1591,1552, 1483, 1415, 1367, 1358, 1342, 1292, 1097, 997, 827, 794, 729, 702, 601, 472 cm-1 ; mass spectrum (EI), m/e 347. Anal. (C 20 H14ClN3O.3/8) Calcd.: C, 67.75; H, 4.19; N, 11.85; Cl, 9.99. Found: C, 67.95; H, 4.09; N, 11.84; Cl, 9.99.

Workup

  1. customwas collected
  2. customdried
  3. customCrystallization from methanol

Sources & evidence

ORD record
ord-ceb2256c03d24ad3ac4eb6ef032a17f2
Source dataset
uspto-grants-1995_11
Patent number
US05466697

Reaction notes

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