Allyl bromide → HCID 12733866, compound

HRID 1578274Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:17])=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[F:18].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>CN(C=O)C>[CH2:27]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([Cl:1])[CH:11]=2)[C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8]1)[CH:26]=[CH2:25]

Participants

Conditions

Temperature: 110 °C

Procedure

13.5 g of 7-chloro-3-ethoxycarbonyl-6-fluoro-4-hydroxyquinoline and 13.8 g of potassium carbonate in 160 cm3 of DMF were stirred and heated at 110° C. for 1 hour in a round-bottomed flask equipped with a reflux condenser. After cooling to 60° C., the solution was treated with 24 g of allyl bromide. The mixture was stirred and heated at 100° C. until the medium was neutral (duration: about 6 hours). The solvent was evaporated off in vacuo, the residue was taken up in 300 cm3 of water and the reaction product was extracted with chloroform (3×100 cm3). The combined organic extracts were washed with water, dried (MgSO4) and evaporated to dryness. The residue was recrystallised from 72 cm3 of isopropanol. 12 g of 1-allyl-7-chloro-3-ethoxycarbonyl-6-fluoro-4-oxo-1,4-dihydroquinoline, m.p.=162°-164° C., were obtained.

Workup

customequipped with a reflux condenser
temperatureAfter cooling to 60° C.
temperatureheated at 100° C. until the medium
customThe solvent was evaporated off in vacuo
extractionthe reaction product was extracted with chloroform (3×100 cm3)
washThe combined organic extracts were washed with water
dry with materialdried (MgSO4)
customevaporated to dryness
customThe residue was recrystallised from 72 cm3 of isopropanol

Sources & evidence

ORD record: ord-22beb637a8e7470b8567e029364f67fe
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04292317

Reaction notes

Loading…