Cesium carbonate → 2-(2-Methoxy-quinolin-8-yloxy)-malonic acid diethyl ester

HRID 1801464Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([OH:13])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.Br[CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:19]([O:18][C:16](=[O:17])[CH:15]([O:13][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11]2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:20]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-methoxy-quinolin-8-ol (commercial; 1.75 g, 10 mmol) and diethyl bromomalonate (1.85 mL, 10 mmol) in DMF (35 mL) was added Cs2CO3 (6.52 g, 20 mmol). The reaction mixture was heated at 80° C. for 1.5 h then allowed to cool to rt. The reaction mixture was filtered and the filtrate concentrated to dryness. The residue was purified by CC (EA-Hept 1:3 to 1:1) to give the title compound as a yellowish oil (2.50 g, 75% yield).

Workup

temperatureto cool to rt
filtrationThe reaction mixture was filtered
concentrationthe filtrate concentrated to dryness
customThe residue was purified by CC (EA-Hept 1:3 to 1:1)

Sources & evidence

ORD record: ord-268da6e708084c3b858c31c3540e7e4e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349828B2

Reaction notes

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