Diethyl Malonate → HCID 178470067, compound

HRID 2276348Notes

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[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=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[CH2:8][CH2:7][CH2:6][CH2:5][C:4]3=[N:3][C:2]=2[N:1]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (2-amino-5,6,7,8-tetrahydroquinolin-3-yl)(p-tolyl)methanone (0.533 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 to 60%) in dichloromethane as eluent to furnish 0.186 g (25%) of ethyl 2-hydroxy-4-(p-tolyl)-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate as a white solid. ESI/APCI(+): 363 (M+H). NMR 1H (DMSO-d6) (ppm): δ 12.37 (s, 1H, NH); 7.35-7.19 (m, 5H, 5×Harom.); 4.00 (q, 2H, OCH2CH3); 2.88 (m, 2H, CH2); 2.66 (m, 2H, CH2); 2.35 (s, 3H, CH3); 1.86-1.79 (m, 2H, CH2); 1.74-1.69 (m, 2H, CH2); 0.90 (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-3f7ea77486424e56bbd1fda9bbcafc21
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09132129B2

Reaction notes

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