Hydroxylamine → 5-Chloro-N'-hydroxy-6-[(2-methoxyethyl)amino]pyridine-3-carboximidamide

HRID 1631009Notes

Reaction equation

HRID 1631009 reaction equation
[NH2:1][OH:2].[Cl:3][C:4]1[C:5]([NH:12][CH2:13][CH2:14][O:15][CH3:16])=[N:6][CH:7]=[C:8]([CH:11]=1)[C:9]#[N:10]>C1COCC1>[Cl:3][C:4]1[CH:11]=[C:8]([C:9](=[N:1][OH:2])[NH2:10])[CH:7]=[N:6][C:5]=1[NH:12][CH2:13][CH2:14][O:15][CH3:16]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 585542235-Chloro-6-[(2-methoxyethyl)amino]nicotinonitrile

Product 1

HCID 768281865-Chloro-N'-hydroxy-6-[(2-methoxyethyl)amino]pyridine-3-carboximidamideYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydroxylamine (5.39 g, 164 mmol) was added into a solution of 5-chloro-6-[(2-methoxyethyl)amino]nicotinonitrile (6.9 g, 32.7 mmol) in THF (70 mL) under nitrogen. The reaction mixture was stirred at RT for 36 hours, and then was concentrated under reduced pressure to afford the title compound as a pale yellow solid (8.2 g, quantitative). LC/MS, M+(ESI): 245.1. 1H NMR (DMSO-d6, 400 MHz) δ 9.49 (1H, s), 8.27 (1H, s), 7.78 (1H, s), 6.57 (1H, t), 5.77 (2H, s), 3.53 (2H, m), 3.46 (2H, m), 3.25 (3H, s).

Workup

  1. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-915365a422af41bfb948136d74b10159
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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