Dimethylformamide → Methyl 4-ethoxy-6-fluoroquinoline-2-carboxylate

HRID 2377796Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH3:15])=[O:13])=[CH:6][C:5]2=[O:16].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.I[CH2:29][CH3:30]>O>[CH2:29]([O:16][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=1)[CH3:30]

Participants

Conditions

Temperature: 50 °C

Procedure

8.0 g (0.036 M) of methyl 6-fluoro-4-oxo-1,4-dihydroquinoline-2-carboxylate and 15.0 g (0.108 M) of potassium carbonate are introduced into 80 ml of DMF. The reaction mixture is stirred for 1 hour at 50° C. After addition of 3.0 ml (0.037 M) of iodoethane and heating for 12 hours at 50° C., the reaction medium is poured into 400 ml of demineralized water. A brown solid precipitates out. The solid is filtered off, washed thoroughly with water and then with isopropyl ether, and finally dried under vacuum at 40° C.

Workup

temperatureheating for 12 hours at 50° C.
customA brown solid precipitates out
filtrationThe solid is filtered off
washwashed thoroughly with water
dry with materialwith isopropyl ether, and finally dried under vacuum at 40° C.

Sources & evidence

ORD record: ord-91e3bb3cb59048bc9cffdde48d63dea7
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470708B2

Reaction notes

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