Water → HCID 9860630, compound

HRID 128941Notes

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+].I[CH2:26][CH3:27].O>CN(C=O)C>[CH2:26]([N:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:17]2[N:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]1=[O:18])[CH3:27]

Participants

Conditions

Temperature: 21 °C

Procedure

To a suspension of 8-(3-chlorophenyl)-1,6-naphthyridin-5-one (128 mg, 0.5 moles) and potassium carbonate (83 mg, 0.6 moles) in 10 ml DMF was added dropwise iodoethane (0.06 ml, 0.75 moles) under an atmosphere of nitrogen. The reaction mixture was stirred overnight at 21° C. The mixture was poured into 50 ml water and after stirring for one hour a white precipitate was collected and dried. Crystallization from ether/hexanes gave 117 mg (82% yield) of the desired 6-ethyl-8-(3-chlorophenyl)-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 127°-128° C.; TLC 1:4 EtOAc/Hex; 1H NMR (CDCl3, 300 MHz) δ1.42 (t, 3H, J= 7.2), 4.11 (q, 2H, J=7.2), 7.35-7.60 (m, 6H), 8.76 (dd, 1H, J=8.0, 1.9), 8.93 (dd, 1H, J=4.5, 1.8); 13C NMR (75 MHz, CDCl3) δ161.54, 154.13, 151.62, 137.15, 136.60, 134.29, 134.16, 129.96, 129.53, 128.24, 127.70, 121.95, 119.63, 108.46, 44.62, 14.67; IR (KBr) vmax 3439, 1647, 1622, 1591, 1564, 1552, 1483, 1458, 1439, 1417, 1375, 1298, 1176, 1167, 1099, 794, 729, 711, 696, 603 cm-1 ; mass spectrum (EI), m/e 284. Anal. (C16H13ClN2O .1/8 H2O) Calcd.: C, 66.96; H, 4.57; N, 9.76. Found: C, 66.82; H, 4.55; N, 9.61.

Workup

stirringafter stirring for one hour a white precipitate
customwas collected
customdried
customCrystallization from ether/hexanes

Sources & evidence

ORD record: ord-69ff925a15884155a80ed9783334b77b
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05466697

Reaction notes

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