Butylamine → HCID 19067885, compound

HRID 1957549Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[C:11]([CH2:20][CH:21]=[CH2:22])[C:12]([OH:19])=[C:13]([CH2:16][CH:17]=[CH2:18])[CH:14]=2)[CH2:9][CH2:8][C:7]1=[O:23].[CH2:24]([NH2:28])[CH2:25][CH2:26][CH3:27]>C(#N)C>[CH2:24]([NH:28][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[C:11]([CH2:20][CH:21]=[CH2:22])[C:12]([OH:19])=[C:13]([CH2:16][CH:17]=[CH2:18])[CH:14]=2)[CH2:9][CH2:8][C:7]1=[O:23])[CH2:25][CH2:26][CH3:27]

Participants

Conditions

Temperature: 80 °C

Procedure

1-(4-Bromobutyl)-5,7-diallyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone (1.9 g) prepared in Example 43 was dissolved in acetonitrile (50 ml), then n-butylamine (2 ml) was added and stirred at 80° C. for 4 hours. The reaction mixture was extracted with ethyl acetate, and the extract was washed with an aqueous solution saturated with sodium bicarbonate, next with water, then concentrated under reduced pressure. Thus obtained oily residual product was dissolved in ethanol, acidified by adding oxalic acid, then concentrated to dryness, and recrystallized from acetone, there was obtained of 1-(4-n-butylaminobutyl)-5,7-diallyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone.oxalate in 35% yield.

Workup

extractionThe reaction mixture was extracted with ethyl acetate
washthe extract was washed with an aqueous solution saturated with sodium bicarbonate, next with water
concentrationconcentrated under reduced pressure
dissolutionThus obtained oily residual product was dissolved in ethanol
additionby adding oxalic acid
concentrationconcentrated to dryness
customrecrystallized from acetone

Sources & evidence

ORD record: ord-1e20cd2be1b245658f4b54e86294144c
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05786367

Reaction notes

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