Ammonium Hydroxide → N-(4-(hydroxymethyl)pyridin-2-yl)acetamide

HRID 426237Notes

Reaction equation

HRID 426237 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([CH2:11][O:12]C(=O)C)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].[OH-].[NH4+]>CO>[OH:12][CH2:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 231508814-Acetoxymethyl-2-acetylaminopyridine

Product 1

HCID 23151114N-(4-(hydroxymethyl)pyridin-2-yl)acetamideYield 101.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid 2-acetylamino-pyridin-4-ylmethyl ester (4.2 g, 20 mmol) was stirred with ammonium hydroxide (10 ml) in methanol (50 ml) at room temperature. After 24 hr., the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA) to afford 3.36 g (quantitative) of N-(4-hydroxymethyl-pyridin-2-yl)-acetamide as a pale yellow solid. m.p. 145° C.; 1H NMR (200 MHz, CDCl3/CD3OD) δ 2.19 (3H, s), 4.67 (2H, s), 7.08 (1H, d, J=5.0 Hz), 8.10 (1H, s), 8.17 (1H, d, J=5.0 Hz).

Workup

  1. custom, the mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, EA)

Sources & evidence

ORD record
ord-74b0f4f33b4f4d9f8eaad8c8ea8668fd
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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