Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]=[CH:7][C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]2[OH:22].C(=O)([O-])[O-].[K+].[K+].[CH2:29](Br)[CH2:30][OH:31]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([CH2:29][CH2:30][OH:31])[CH:7]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22]Participants
5
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 2 g (0.0076 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-caboxylate and 1.85 g (2×0.0076 mol) of potassium carbonate in 20 ml of dimethylformamide is heated for 30 minutes at 60° C. and left to cool, 3.35 g (4×0.0076 mol) of ethylene bromohydrin are added, the mixture is heated at 80°-90° C. for 10 hours, active carbon is added, the mixture is filtered hot, the filtrate is evaporated to dryness, water is added and the precipitate formed is filtered off and washed with water. It is recrystallized from dimethylformamide to give 1.2 g of a solid melting at 237°-239° C.
Workup
- waitleft
- temperatureto cool
- temperaturethe mixture is heated at 80°-90° C. for 10 hours
- additionactive carbon is added
- filtrationthe mixture is filtered hot
- customthe filtrate is evaporated to dryness, water
- additionis added
- customthe precipitate formed
- filtrationis filtered off
- washwashed with water
- customIt is recrystallized from dimethylformamide
Sources & evidence
- ORD record
- ord-d71e37624aff4110a72e833bc5f49268
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04727080
Linked notes
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