Pyridine-2-carboxylic acid (2-acetyl-5-methoxy-phenyl)-amide → HCID 178487680, compound

HRID 1815717

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[NH:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)=O)(=[O:3])[CH3:2].CC([O-])(C)C.[K+].C1COCC1>C1COCC1>[CH3:11][O:10][C:7]1[CH:6]=[C:5]2[C:4]([C:1]([OH:3])=[CH:2][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:12]2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension suspension of Pyridine-2-carboxylic acid (2-acetyl-5-methoxy-phenyl)-amide (2.90 g, 10.7 mmol) in THF (50 mL) was added t-BuOK/THF (1M, 24 mL, 24 mmol). The reaction mixture was heated at 70° C. for 3 h and stirred overnite. The solvent was removed the in vacuo. Cold water was added to the residue and adjusted pH to 4.6 with aqueous 1.0 N HCl, filtered. The solid residue was purified over a Biotage 65M column (MeOH/CH2Cl2: 0 to 15%) to provide the product (2.26 g, 84%): LC-MS (retention time: 1.19, Method D), MS m/z 253 (M++1).

Workup

customThe solvent was removed the in vacuo
additionCold water was added to the residue
filtrationfiltered
customThe solid residue was purified over a Biotage 65M column (MeOH/CH2Cl2: 0 to 15%)

Sources & evidence

ORD record: ord-8c0bb5369505440292556db4d2c7c5ae
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878722B2

Linked notes

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