Hydrochloric Acid → N-((6-chloropyridin-3-yl)methyl)-N-ethyl-2-methyl-4-nitro-8-oxa-2-aza-bicyclo[3.2.1]oct-3-en-3-amine

HRID 1043519Notes

Reaction equation

HRID 1043519 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:17][CH3:18])[C:10]([NH:15][CH3:16])=[CH:11][N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.[CH:19](=[O:24])[CH2:20][CH2:21][CH:22]=O.Cl>C(#N)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:17][CH3:18])[C:10]2[N:15]([CH3:16])[CH:22]3[O:24][CH:19]([C:11]=2[N+:12]([O-:14])=[O:13])[CH2:20][CH2:21]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12524ButanedialHCID 86457N-((6-Chloro-3-pyridinyl)methyl)-N-ethyl-N'-methyl-2-nitro-1,1-ethenediamine

Product 1

HCID 58496253N-((6-chloropyridin-3-yl)methyl)-N-ethyl-2-methyl-4-nitro-8-oxa-2-aza-bicyclo[3.2.1]oct-3-en-3-amineYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 50 ml round bottom flask was added 1.35 g (0.005 mol) N-((6-chloropyridin-3-yl)methyl)-N-ethyl-N′-methyl-2-nitroethene-1,1-diamine, 30 ml dry acetonitrile, 0.860 g (0.01 mol) succinaldehyde and catalytic concentrated HCl. The reaction was stirred at r.t. and monitored by TLC. After completion, the mixture was evaporated to remove solvent and purified by column chromatography to afford final product as faint yellow powder with 40% yield.

Workup

  1. customAfter completion, the mixture was evaporated
  2. customto remove solvent
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-91bba571e5844645b9cdff758538430c
Source dataset
uspto-grants-2013_10
Patent number
US08563546B2

Reaction notes

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