Sulfuric Acid → N-(5-chloro-2-oxo-1,2-dihydro-pyridin-4-ylmethyl)-acetamide
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10](=[O:12])[CH3:11])[C:5]([Cl:13])=[CH:4][N:3]=1.[OH:14]S(O)(=O)=O.[NH4+].[OH-]>O>[Cl:13][C:5]1[C:6]([CH2:8][NH:9][C:10](=[O:12])[CH3:11])=[CH:7][C:2](=[O:14])[NH:3][CH:4]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
Compound N-(2,5-dichloro-pyridin-4-ylmethyl)-acetamide (250 mg, 1.14 mmol) was added to 33% H2SO4 (3 mL) and the mixture heated in a CEM microwave reactor at 200° C. for 30 min. After cooling to room temperature, the reaction mixture was diluted with water (20 mL) and basified with excess concentrated NH4OH. The reaction mixture was then frozen using a dry ice/acetone bath and evaporated to dryness in vacuo overnight in a freeze-dry apparatus. The solids were purified by column chromatography using a 12 g ISCO combi-flash column and dry-loading cartridge (silica gel, 100:0 to 50:50 DCM:DCM/MeOH/NH4OH 6:3:1) to afford N-(5-chloro-2-oxo-1,2-dihydro-pyridin-4-ylmethyl)-acetamide (246 mg, quant.) as an off-white solid. This material was directly in the next step.
Workup
- temperatureAfter cooling to room temperature
- temperatureThe reaction mixture was then frozen
- customevaporated to dryness in vacuo overnight in a freeze-dry apparatus
- customThe solids were purified by column chromatography
- dry with materialdry-loading cartridge (silica gel, 100:0 to 50:50 DCM:DCM/MeOH/NH4OH 6:3:1)
Sources & evidence
- ORD record
- ord-e702dc0a00524a38aacd5d8567ac6a17
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601714B2
Reaction notes
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