Hydrochloric Acid → 2-methyl-4-(trifluoromethyl)aniline hydrochloride
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12]C(=O)C.[ClH:16].CC1C=C(C(F)(F)F)C=CC=1N>C(O)C>[ClH:16].[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[NH2:12]Participants
5
Procedure
A solution of N-[2-methyl-4-(trifluoromethyl)phenyl]acetamide (5.17 g) and aqueous hydrochloric acid (37%, 12 mL) in ethanol (24 mL) was heated to reflux for 3 hours and then stirred at ambient temperature for 48 hours. GC analysis of the reaction mixture showed a 98:2 peak area ratio of 2-methyl-4-(trifluoromethyl)aniline to starting material. 2-Methyl-4-(trifluoromethyl)aniline hydrochloride was obtained as a white solid by filtering the reaction mixture and washing the solids with ethyl acetate. A second crop of 2-methyl-4-(trifluoromethyl)aniline hydrochloride was obtained by evaporating the filtrate to dryness, triturating the residue in ethyl acetate, then filtering, providing a total of 4.27 g (85% yield).
Workup
- temperatureto reflux for 3 hours
Sources & evidence
- ORD record
- ord-d921fd13fd9a4c008a064028f57cdc02
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07145035B2
Reaction notes
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