O-(propan-2-yl)hydroxylamine hydrochloride → HCID 67506941, compound

HRID 2105473Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:12][C:13](=O)[C:14]([CH3:17])([CH3:16])[CH3:15].Cl.[CH:20]([O:23][NH2:24])([CH3:22])[CH3:21]>C(O)(C)C>[C:14]([C:13]1[N:24]([O:23][CH:20]([CH3:22])[CH3:21])[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 80 °C

Procedure

Under a nitrogen atmosphere, a mixture of N-(4-chloroquinolin-3-yl)trimethylacetamide (6.00 g, 1 eq), O-isopropylhydroxylamine hydrochloride (7.6 g, 3 eq), and anhydrous isopropanol (80 mL) was heated at 80° C. for 19 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane, washed sequentially with saturated aqueous potassium carbonate, water, and brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified by column chromatography (150 g of silica gel eluted with a gradient of 20-55% ethyl acetate in dichloromethane) to provide 2.8 g of 2-tert-butyl-1-isopropoxy-1H-imidazo[4,5-c]quinoline as a brown oil.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
dissolutionThe residue was dissolved in dichloromethane
washwashed sequentially with saturated aqueous potassium carbonate, water, and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (150 g of silica gel
washeluted with a gradient of 20-55% ethyl acetate in dichloromethane)

Sources & evidence

ORD record: ord-7aac3ae661b5484cb196eb7001569128
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579359B2

Reaction notes

Loading…