Acetohydroxamic Acid → HCID 59383899, compound
Reaction equation
CC(C)([O-])C.[K+].[OH:7][NH:8][C:9](=O)[CH3:10].F[C:13]1[C:20]([I:21])=[C:19]([CH3:22])[CH:18]=[CH:17]C=1C#N.C[N:24](C=O)C>>[I:21][C:20]1[C:13]2[O:7][N:8]=[C:9]([NH2:24])[C:10]=2[CH:17]=[CH:18][C:19]=1[CH3:22]Participants
Procedure
Potassium tert-butoxide (2.20 g, 19.2 mmol) was added to a solution of N-hydroxyacetamide (1.44 g, 19.2 mmol) in N,N′-dimethylformamide (25 mL) under argon. The resulting white suspension was stirred at room temperature for 30 minutes and then 2-fluoro-3-iodo-4-methylbenzonitrile (WO2006094187, 2.00 g, 7.7 mmol) was added and the mixture was stirred at room temperature for 6 hours. Further N-hydroxyacetamide (0.29 g, 3.9 mmol) and potassium tert-butoxide (0.45 g, 3.9 mmol) were added and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and water and ethyl acetate were added. The organic layer was separated and the aqueous phase was extracted with further ethyl acetate. The combined organic layers were washed with brine, dried, (MgSO4) and evaporated. The residue was purified by flash chromatography (9:1 hexanes/ethyl acetate to ethyl acetate) to yield the title compound (1.79 g, 81%) as a solid.
Workup
- stirringthe mixture was stirred at room temperature for 6 hours
- stirringthe mixture was stirred at room temperature overnight
- customThe solvent was evaporated under reduced pressure and water and ethyl acetate
- additionwere added
- customThe organic layer was separated
- extractionthe aqueous phase was extracted with further ethyl acetate
- washThe combined organic layers were washed with brine
- customdried
- custom(MgSO4) and evaporated
- customThe residue was purified by flash chromatography (9:1 hexanes/ethyl acetate to ethyl acetate)
Sources & evidence
- ORD record
- ord-8111a3c02c2848f4a0b1543822d6a961
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450341B2
Reaction notes
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