1,4-Dioxane hydrochloride → Ethyl 2-(6-(methylamino)pyridin-2-yl)acetate

HRID 1369201Notes

Reaction equation

HRID 1369201 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][CH2:13]C(OC(C)(C)C)=O)[N:7]=1)[CH3:2].Cl.O1CCOCC1>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][CH3:13])[N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 22496030Ethyl-6-[(tert-butoxycarbonyl)methylamino]-2-pyridylacetate

Product 1

HCID 22507068Ethyl 2-(6-(methylamino)pyridin-2-yl)acetateYield 119.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl-6-[(tert-butoxycarbonyl)methylamino]-2-pyridylacetate (10.72 g, 36.42 mmole) in anhydrous dioxane (91 mL) was cooled to the point of partial crystallization of the solvent, and 4 M HCl/dioxane (91 mL, 364.2 mmole) was added. The solution was warmed to RT and stirred for 17 hr, then was concentrated. The resulting light yellow solid was slurried with CH2Cl2/toluene and reconcentrated to leave the title compound (8.48 g, quantitative) as a light yellow powder: 1H NMR (250 MHz, CD3OD) δ7.84 (dd, J=9.0, 7.2 Hz, 1 H), 6.96 (d, J=9.0 Hz, 1 H), 6.78 (d, J=7.2 Hz, 1 H), 4.22 (q, J=7.1 Hz, 2 H), 3.93 (s, 2 H), 3.05 (s, 3 H), 1.27 (t, J=7.1 Hz, 3 H); MS (ES) m/e 195 (M+H)+.

Workup

  1. additionwas added
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-736923f8e3304ffca11c85294248cef5
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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