Diethyl Malonate → HCID 178470068, compound

HRID 2276346Notes

Reaction equation

[NH2:1][C:2]1[C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:21](OCC)(=[O:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[O-]CC.[Na+]>C(O)C>[OH:28][C:21]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:11]2[CH:10]=[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]3=[N:3][C:2]=2[N:1]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (2-aminoquinolin-3-yl)(p-tolyl)methanone (0.525 g; 2 mmol) and diethyl malonate (1.22 mL; 8 mmol) in ethanol (10 mL) under nitrogen atmosphere was added a solution of sodium ethoxide 21% (w/w) in ethanol (2.24 mL; 6 mmol). The mixture was stirred in a sealed tube and heated to 100° C. for 48 h. The volatiles were removed under reduced pressure and the remaining residue was purified by flash-chromatography on silica gel column using a gradient of ethyl acetate (1-60%) in dichloromethane as eluent to furnish 0.217 g (30%) of ethyl 2-hydroxy-4-p-tolylbenzo[b][1,8]naphthyridine-3-carboxylate as a bright yellow solid. ESI/APCI(+): 359 (M+H). NMR 1H (DMSO-d6) (ppm): δ 12.54 (s, 1H, NH); 8.21 (s, 1H, Harom.); 8.03 (d, 1H, Harom.); 7.93-7.80 (m, 2H, 2×Harom.); 7.51-7.46 (m, 1H, Harom.); 7.41-7.32 (m, 4H, 4×Harom.); 4.02 (q, 2H, OCH2CH3); 2.43 (s, 3H, CH3); 0.94 (t, 3H, OCH2CH3).

Workup

customThe volatiles were removed under reduced pressure
customthe remaining residue was purified by flash-chromatography on silica gel column

Sources & evidence

ORD record: ord-43209ac836184308a3b0058f4a3b2ddf
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09132129B2

Reaction notes

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