Ammonium Chloride → HCID 59031753, compound

HRID 505644Notes

Reaction equation

[O:1]1[C@H:7]2[C@@H:2]1[C:3]([CH3:17])([CH3:16])[O:4][C:5]1[C:11]([CH3:12])=[C:10]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:8][C:6]=12.Cl([O-])(=O)(=O)=O.[Li+].[Cl-].[NH4+:25]>O1CCOCC1>[CH3:16][C:3]1([CH3:17])[C@H:2]([OH:1])[C@@H:7]([NH:25][CH2:2][CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:5]=2)[C:6]2[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[C:11]([CH3:12])[C:5]=2[O:4]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (3R*,4R*)-3,4-epoxy-2,2,8-trimethyl-7-nitro-3,4-dihydro-2H-1-benzopyran (600 mg, 2.55 mmol) in 1,4-dioxane (1.2 mL), lithium perchlorate (271 mg, 2.55 mmol) and 2-(phenylethyl)amine (0.384 mL, 3.06 mmol) were added at room temperature and the mixture was stirred at 80° C. for 1 hour. Upon the completion of the reaction, saturated ammonium chloride was added to the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was purified by column chromatography (hexane/ethyl acetate=4/1) and the aimed product was obtained as orange oily substance (yield: 99%).

Workup

additionwas added to the reaction solution
extractionthe resulting solution was extracted with ethyl acetate
washThe organic phase was washed with saturated sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
distillationAfter distilling off the solvent
customthe residue was purified by column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-6becf64cec2348cf86202c77d7245a7d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781483B2

Reaction notes

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