N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-2,2-dimethyl-propionamide → 4-(2-Chlorophenyl)pyridin-3-amine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH:14]C(=O)C(C)(C)C>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH2:14]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 92.5 °C
Procedure
A suspension of 22.2 g (77 mmol) N-[4-(2-chloro-phenyl)-pyridin-3-yl]-2,2-dimethyl-propionamide in 730 ml 3 N hydrochloric acid solution was heated to 90-95° C. overnight. The reaction mixture was cooled to room temperature, washed with three 130 ml portions diethyl ether and 500 ml ethyl acetate were added. The aqueous phase was adjusted to pH 7-8 by addition of 28% sodium hydroxide solution under ice cooling. The organic phase was separated and the product was extracted with three 200 ml portions of ethyl acetate. The combined organic layers were dried (magnesium sulfate) and evaporated to give 14.9 g (95%) of the title compound as white crystals.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- washwashed with three 130 ml portions diethyl ether and 500 ml ethyl acetate
- additionwere added
- additionThe aqueous phase was adjusted to pH 7-8 by addition of 28% sodium hydroxide solution under ice cooling
- customThe organic phase was separated
- extractionthe product was extracted with three 200 ml portions of ethyl acetate
- dry with materialThe combined organic layers were dried (magnesium sulfate)
- customevaporated
Sources & evidence
- ORD record
- ord-aa1e10b85d444d7ca47bb55218a2a504
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06297375B1
Reaction notes
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