Hydroxylamine → Tert-butyl ({5-[amino(hydroxyimino)methyl]-3-chloropyridin-2-yl}amino)acetate

HRID 1631012Notes

Reaction equation

HRID 1631012 reaction equation
[NH2:1][OH:2].[Cl:3][C:4]1[C:5]([NH:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N:6][CH:7]=[C:8]([C:10]#[N:11])[CH:9]=1>C1COCC1>[NH2:11][C:10](=[N:1][OH:2])[C:8]1[CH:9]=[C:4]([Cl:3])[C:5]([NH:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58554110Tert-butyl [(3-chloro-5-cyanopyridin-2-yl)amino]acetate

Product 1

HCID 76828193Tert-butyl ({5-[amino(hydroxyimino)methyl]-3-chloropyridin-2-yl}amino)acetateYield 101%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydroxylamine (1.5 mL, 39.5 mmol) was added into a solution of tert-butyl [(3-chloro-5-cyanopyridin-2-yl)amino]acetate (2.1 g, 7.9 mmol) in THF (30 mL) under nitrogen. The reaction mixture was stirred at RT for 48 hours, and then was concentrated under reduced pressure to afford the title compound as a white solid (2.4 g, quantitative). LC/MS, M+(ESI): 301.0. 1H NMR (DMSO-d6, 400 MHz) δ 9.52 (1H, s), 8.24 (1H, d), 7.81 (1H, d), 7.04 (1H, t), 5.80 (2H, s), 3.95 (2H, m), 1.37 (9H, s).

Workup

  1. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-52df734da1cd4fc7a22108b0804007e3
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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