N-(2-aminoethyl)acetamide → N-(2-(6-chloro-3-nitropyridin-2-ylamino)ethyl)acetamide

HRID 1684990Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.C(N(CC)C(C)C)(C)C.[C:21]([NH:24][CH2:25][CH2:26][NH2:27])(=[O:23])[CH3:22]>C1COCC1>[Cl:11][C:4]1[N:3]=[C:2]([NH:27][CH2:26][CH2:25][NH:24][C:21](=[O:23])[CH3:22])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3.0 g (15.5 mmol) 2,6-dichloro-3-nitropyridine in 50 mL of THF at −78° C. under Ar atmosphere was added 2.7 mL (15.5 mmol) of N,N-diisopropylethyl amine followed by 1.6 mL (15.5 mmol) of N-acetylethylenediamine. The mixture was stirred at −78° C. for 30 min, allowed to warm to room temperature, and stirred for 72 hours. The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with MeOH/dichloromethane gradient (1→10%) to provide N-(2-(6-chloro-3-nitropyridin-2-ylamino)ethyl)acetamide as pale yellow solid.

Workup

temperatureto warm to room temperature
stirringstirred for 72 hours
customThe solvent was removed in vacuo
customthe residue was purified by flash chromatography
washeluting with MeOH/dichloromethane gradient (1→10%)

Sources & evidence

ORD record: ord-2f8a89f695274403ad0ae4919860c78c
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148376B2

Reaction notes

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