Ammonia → 6-Chloro-5-(trifluoromethyl)pyridin-2-amine
Reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[NH3:13]>>[Cl:1][C:2]1[N:3]=[C:4]([NH2:13])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9]Participants
3
Conditions
- Temperature
- 93 °C
Procedure
2,6-Dichloro-3-(trifluoromethyl)pyridine (5.00 g, 23.2 mmol) and 28% aqueous ammonia (150 mL) were placed in a 250 mL autoclave. The mixture was heated at 93° C. for 21 h. The reaction was cooled to rt and extracted with EtOAc (100 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (2-20% EtOAc in petroleum ether as eluant) to give 6-chloro-5-(trifluoromethyl)pyridin-2-amine (2.1 g, 46% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.69 (d, J=8.4 Hz, 1H), 7.13 (br s, 2H), 6.43 (d, J=8.4 Hz, 1H). MS (ESI) m/z (M+H)+ 197.2
Workup
- temperatureThe reaction was cooled to rt
- extractionextracted with EtOAc (100 mL×3)
- dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
- customevaporated under vacuum
- customto give the crude product, which
- customwas purified by column chromatography on silica gel (2-20% EtOAc in petroleum ether as eluant)
Sources & evidence
- ORD record
- ord-c2878f54311642ae90d9e299a90b11b1
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07659268B2
Reaction notes
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