Hydrochloric Acid → 1-(4-Aminophenyl)-3-allyl-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 1904799Notes

Reaction equation

C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]23[CH2:16][CH:15]2[C:14](=[O:17])[N:13]([CH2:18][CH:19]=[CH2:20])[C:12]3=[O:21])=[CH:7][CH:6]=1)(=O)C.Cl.[OH-].[Na+]>O>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]23[CH2:16][CH:15]2[C:14](=[O:17])[N:13]([CH2:18][CH:19]=[CH2:20])[C:12]3=[O:21])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2.2 g of 1-(4-acetylaminophenyl)-3-allyl-3-azabicyclo[3.1.0]hexane-2,4-dione, 8 ml of water and 8 ml of concentrated hydrochloric acid is stirred for 3 hours at 100° C. The mixture is diluted with a small amount of water, cooled in an ice-water bath, made alkaline with 30% sodium hydroxide solution, and extracted twice with ethyl acetate. The organic phases are washed repeatedly with water and once with a concentrated aqueous solution of sodium chloride, dried over magnesium sulfate and filtered. The filtrate is concentrated and the residue is crystallised from ethyl acetate/petroleum ether. The title compound is obtained in the form of pale beige-coloured crystals with m.p. 104°-106° C. and with Rf=0.57 on thin-layer silica gel plates in the system methylene chloride/methanol (10:1).

Workup

temperaturecooled in an ice-water bath
extractionextracted twice with ethyl acetate
washThe organic phases are washed repeatedly with water and once with a concentrated aqueous solution of sodium chloride
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationThe filtrate is concentrated
customthe residue is crystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record: ord-8b1860a83be64604aebe7d58b4c1e64f
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04839379

Reaction notes

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