Ethyl (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate → Ethyl 3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)propionate

HRID 2174581Notes

Reaction equation

[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][C:7](/[CH:12]=[CH:13]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][C:5]=2[CH2:4][CH2:3]1>CO.[Pd]>[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][C:7]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][C:5]=2[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 27.5 °C

Procedure

To a stirred solution of 49a (7.7 g, 34.3 mmol) in methanol (150 ml) was added 10% Pd/C (3 g) under nitrogen. The reaction mixture was stirred in presence of H2 gas at 20-35° C. for 16 h. The progress of the reaction was monitored by TLC. After the reaction was completed, the reaction mixture was filtered through celite and concentrated to get the desired compound as a white solid (7 g, 90.2%); 1H NMR (400 MHz, DMSO-d6) δ 10.35 (s, 1H), 7.95 (s, 1H), 7.48 (s, 1H), 4.05 (q, J=7.1 Hz, 2H), 2.83 (t, J=7.6 Hz, 2H), 2.79-2.60 (m, 4H), 2.58-2.55 (m, 2H), 1.16 (m, 3H); MS (ES) m/e 249.1 (M+H)+.

Workup

filtrationthe reaction mixture was filtered through celite
concentrationconcentrated

Sources & evidence

ORD record: ord-190efa89e84a4bd39453bc06e14a1bc5
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062002B2

Reaction notes

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