Tert-butyl {2-[(1-chloro-6-cyanonaphthalen-2-yl)oxy]ethyl}carbamate → 2-[(1-Chloro-6-cyanonaphthalen-2-yl)oxy]ethanaminium chloride

HRID 1400302Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:14][CH2:15][CH2:16][NH:17]C(=O)OC(C)(C)C>C(OCC)C.Cl.O1CCOCC1>[Cl-:1].[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:14][CH2:15][CH2:16][NH3+:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) single necked flask containing a solution of tert-butyl {2-[(1-chloro-6-cyanonaphthalen-2-yl)oxy]ethyl}carbamate in 3 mL of ethyl ether, 5 mL of 4 M HCl solution in dioxane were added. The resulting mixture was stirred at room temperature overnight. The solution was concentrated under reduce pressure to afford 2-[(1-chloro-6-cyanonaphthalen-2-yl)oxy]ethanaminium chloride as a white solid (95% yield).

Workup

additionwere added
concentrationThe solution was concentrated

Sources & evidence

ORD record: ord-7d2651051a34422ea6a3ba1e24275a06
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906946B2

Reaction notes

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