Acrylic Acid → N-[2-(Trifluoromethyl)phenyl]-β-alanine
Reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[F:6][C:7]([F:16])([F:15])[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10]>>[F:6][C:7]([F:15])([F:16])[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][CH2:3][CH2:2][C:1]([OH:5])=[O:4]Participants
3
Conditions
- Temperature
- 75 °C
Procedure
672 g of acrylic acid were added to 500 g of o-trifluoromethylaniline at 20°-25° C. with stirring while bubbling nitrogen therethrough and then 0.5 g of hydroquinone were added thereto in the dark. The mixture was heated to 75° C. over one hour and was then held at 75° C. for 32 hours. The mixture was cooled to 65°-70° C. and 500 ml of technical cyclohexane and 500 ml ofdemineralized water were rapidly added thereto. The mixture was refluxed for 10 minutes and was then slowly cooled to 2° to 4° C. andheld there for one hour. The mixture was vacuum filtered and the recovered crystals were washed and dried to obtain 636.7 g of β-(o-trifluoromethylanilino)-propanoic acid.
Workup
- customwhile bubbling nitrogen
- addition0.5 g of hydroquinone were added
- temperatureThe mixture was cooled to 65°-70° C.
- addition500 ml of technical cyclohexane and 500 ml ofdemineralized water were rapidly added
- temperatureThe mixture was refluxed for 10 minutes
- temperaturewas then slowly cooled to 2° to 4° C. andheld there for one hour
- filtrationfiltered
- washthe recovered crystals were washed
- customdried
Sources & evidence
- ORD record
- ord-fd9ce261a72d4dfdbb03661c6d8051df
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04277607
Reaction notes
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