Allyl bromide → 1-(2-Propen-1-yl)-7-(2-propen-1-yloxy)-1,8-naphthyridin-2(1H)-one

HRID 656884Notes

Reaction equation

[NH:1]1[C:10]2[NH:9][C:8](=[O:11])[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][C:2]1=[O:12].[H-].[Na+].[CH2:15](Br)[CH:16]=[CH2:17].[CH2:19](I)[CH:20]=[CH2:21]>CN(C=O)C>[CH2:15]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:21][CH:20]=[CH2:19])[N:9]=2)[CH:4]=[CH:3][C:2]1=[O:12])[CH:16]=[CH2:17]

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of 1,8-naphthyridine-2,7(1H,8H)-dione (8.0 g, 49.4 mmol)(prepared according to the method of Newkome, George R et al, Journal of Organic Chemistry (1981), 46(5), 833-9) in DMF (200 ml) was treated under argon with sodium hydride (2.2 g of 60% dispersion with mineral oil, 1.3 g, 55 mmol) then heated to 40° C. for 20 minutes. Allyl bromide (˜5 ml) was added. After 2 hours at 40° C. more sodium hydride (2.2 g of 60% dispersion with mineral oil, 1.3 g, 55 mmol) and allyl iodide (˜5 ml) were added. After a further 1 hour at 40° C. the mixture was cooled to room temperature and quenched with saturated aqueous ammonium chloride (5 ml). The mixture was evaporated and the residue chromatographed eluting with 0-10% ethyl acetate in hexane affording the product as a yellow oil (5.2 g, 45%).

Workup

customprepared
temperatureAfter a further 1 hour at 40° C. the mixture was cooled to room temperature
customquenched with saturated aqueous ammonium chloride (5 ml)
customThe mixture was evaporated
customthe residue chromatographed
washeluting with 0-10% ethyl acetate in hexane affording the product as a yellow oil (5.2 g, 45%)

Sources & evidence

ORD record: ord-e81242b32ef4461ba484dd23a1427909
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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