Ethyl bromoacetate → Ethyl 2-(2-iminopyridin-1(2H)-yl)acetate hydrobromide

Reaction equation

[Br:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1>>[BrH:1].[CH2:6]([O:5][C:3](=[O:4])[CH2:2][N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]1=[NH:8])[CH3:7]

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 104392-Aminopyridine

Product 1

HCID 68699194Ethyl 2-(2-iminopyridin-1(2H)-yl)acetate hydrobromide

Procedure

To 39 mL (0.35 mol) of ethyl bromoacetate is added 9.4 g (0.1 mol) of 2-aminopyridine portionwise at 0° C. The resulting mixture is allowed to warm to room temperature and stirred at this temperature for 30 minutes. The precipitate is collected and washed with hexane to give the desired compound as light tan solid.

Workup

customThe precipitate is collected
washwashed with hexane

Sources & evidence

ORD record: ord-139322c54df1428e9f9697ab542f9be2
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193214B2

Reaction notes

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