4-Chloroaniline → Propanamide, N-(4-chlorophenyl)-2,2-dimethyl-
Reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1>N1C=CC=CC=1>[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])=[CH:11][CH:10]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Trimethylacetyl chloride (35 g) was added drop wise to a solution of 4-chloroaniline (31.9 g) in dry pyridine and the reaction was stirred under nitrogen overnight. About half of the pyridine was removed by rotary evaporation, then the mixture was treated with 6M hydrochloric acid and extracted with ethyl acetate. The extracts were washed with saturated aqueous NaHCO3 and with water, then were dried (MgSO4), filtered and concentrated by rotary evaporation. The resulting crystalline product was vacuum filtered and dried at high vacuum to constant weight, resulting in a good yield of N-(4-chloro-phenyl)-2,2-dimethyl-propionamide as fine needles. EDC (10 g) and 2-methyl-nicotinic acid (7.15 g) were magnetically stirred in acetonitrile-THF with N,O-dimethylhydroxylamine hydrochloride (9.75 g) and triethylamine (25 mL). After stirring overnight at ambient temperature, the resulting white suspension was added to ice water and extracted with ethyl acetate (3×100 mL). The extracts were dried, filtered, and concentrated to give a light amber oil.
Workup
- customAbout half of the pyridine was removed by rotary evaporation
- additionthe mixture was treated with 6M hydrochloric acid
- extractionextracted with ethyl acetate
- washThe extracts were washed with saturated aqueous NaHCO3 and with water
- dry with materialwere dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
- filtrationfiltered
- customdried at high vacuum to constant weight
Sources & evidence
- ORD record
- ord-3bbd3ec27ba74a43a655b72a45bcd35f
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420055B2
Reaction notes
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