Ammonium Hydroxide → N-(4-(hydroxymethyl)pyridin-2-yl)acetamide
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- custom, the mixture was evaporated in vacuo
- 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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