N,N-Dimethylaniline → 6-Allyl-5-hydroxy-3,8-dimethylcarbostyril

HRID 1900809Notes

Reaction equation

CN(C)[C:3]1[CH:8]=CC=C[CH:4]=1.C([O:13][C:14]1[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]2[C:15]=1[CH:16]=[C:17]([CH3:26])[C:18](=[O:25])[NH:19]2)C=C>CCCCCC>[CH2:8]([C:23]1[C:14]([OH:13])=[C:15]2[C:20](=[C:21]([CH3:24])[CH:22]=1)[NH:19][C:18](=[O:25])[C:17]([CH3:26])=[CH:16]2)[CH:3]=[CH2:4]

Participants

Conditions

Temperature: 200 °C

Procedure

N,N-dimethylaniline (10 ml) was added to 5-allyloxy-3,8-dimethylcarbostyril (4.32 g, 18.9 mmol), and stirred for 2 hours and 40 minutes in a bath of 200° C. in the atmosphere of argon. After cooling, hexane was added. Precipitated crystals were collected by filtration, and purified by silica gel chromatography (chloroform:methanol =10:1). The purified product was subjected to recrystallization (chloroform-n-hexane) to obtain 3.86 g of the title compound as colorless crystals (89.4%).

Workup

temperatureAfter cooling
customPrecipitated crystals
filtrationwere collected by filtration
custompurified by silica gel chromatography (chloroform:methanol =10:1)
customThe purified product was subjected to recrystallization (chloroform-n-hexane)

Sources & evidence

ORD record: ord-e7ebc4ed6eb9486097ed9b57d042e59f
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576324

Reaction notes

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