Ethyl 3-chloro-3-oxopropionate → 6-Chloro-1-(4-methoxy-benzyl)-4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid ethyl ester

HRID 1745852Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.[CH2:21]([O:23][C:24](=[O:29])[CH2:25][C:26](Cl)=[O:27])[CH3:22].CC[O-].[Na+]>C1C=CC=CC=1.O>[CH2:21]([O:23][C:24]([C:25]1[C:26](=[O:27])[N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C:5]2[C:6]([C:8]=1[CH3:9])=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:29])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2 (0.20 g, 1.18 mmol) in 3 mL of anhydrous benzene was treated with ethyl-3-chloro-3-oxopropionate (165 μL, 0.20 g, 1.30 mmol). The reaction mixture was heated to 80° C. for 1 h. The reaction was allowed to cool to room temperature and was concentrated in vacuo. The resulting oil was dissolved in 3 mL of ethanol, treated with NaOEt (40.0 mg, 0.59 mmol). The suspension was heated to 80° C. for 10 min, allowed to cool to room temperature, and diluted with H2O. The resulting white precipitate was filtered to give 3 (0.38 g, 80%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.69 (d, J=2.3 Hz, 1H), 7.39 (dd, J=2.3, 9 Hz, 1H), 7.26 (d, J=9 Hz, 1H), 7.15 (d, J=8.6 Hz, 2H), 6.81 (d, j=8.6 Hz, 2H), 5.47 (br S, 2H), 4.46 (q, J=7.2 Hz, 2H), 3.75 (s, 3H), 2.46 (s, 3H), 1.43 (t, J=7.2 Hz, 3H).

Workup

temperatureto cool to room temperature
concentrationwas concentrated in vacuo
dissolutionThe resulting oil was dissolved in 3 mL of ethanol
temperatureThe suspension was heated to 80° C. for 10 min
temperatureto cool to room temperature
filtrationThe resulting white precipitate was filtered

Sources & evidence

ORD record: ord-c0049d8151ab4f01931eaebcd1a05a6e
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07019141B2

Reaction notes

Loading…