Imidazole → O,N-Dimethyl-2-(imidazol-1-yl)pyridine-5-hydroxamic acid

HRID 850102Notes

Reaction equation

[CH3:1][O:2][N:3]([CH3:13])[C:4]([C:6]1[CH:7]=[CH:8][C:9](Cl)=[N:10][CH:11]=1)=[O:5].[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[CH3:1][O:2][N:3]([CH3:13])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[N:10][CH:11]=1)=[O:5]

Participants

Conditions

Temperature: 140 °C

Procedure

A suspension of O,N-dimethyl-2-chloropyridine-5-hydroxamic acid (10.0 g, 50 mmol-see Preparation 22(i)), imidazole (4.1 g, 60 mmol) and potassium carbonate (6.9 g, 50 mmol) in N,N-dimethylacetamide (200 ml) was stirred at 140° C. for 24 hours. The mixture was evaporated under reduced pressure and the residue was partitioned between dichloromethane (100 ml) and water (100 ml). The organic phase was washed with water (100 ml) and brine (50 ml) then dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica using gradient elution with ethyl acetate/hexane (1:1,1:0). Fractions containing the desired product were combined and evaporated under reduced pressure to give the title compound (8.2 g, 71%) as an orange oil. A sample was triturated with ether to afford a colourless solid, m.p. 69-70° C.

Workup

customThe mixture was evaporated under reduced pressure
customthe residue was partitioned between dichloromethane (100 ml) and water (100 ml)
washThe organic phase was washed with water (100 ml) and brine (50 ml)
dry with materialthen dried (MgSO4)
customevaporated under reduced pressure
customThe crude product was purified by column chromatography on silica using gradient elution with ethyl acetate/hexane (1:1,1:0)
additionFractions containing the desired product
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-d9279c9db9ee4eb3905994e7449e1265
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015825

Reaction notes

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