Isopropanol → 2-Chloro-4-fluoro-3-methylaniline
Reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([F:11])[C:3]=1[CH3:12].C(O)(C)C>Cl.O>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([F:11])[CH:5]=[CH:6][C:7]=1[NH2:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 82 °C
Procedure
To a mixture of 2-chloro-6-fluoro-3-nitrotoluene (140 g), isopropanol (560 ml) and water (147 ml), hydrogen reduced iron (172.2 g) was added hydrochloric acid (43 drops) and with vigorous stirring the whole heated to reflux temperature (82° C.) for 4 hours. The cooled mixture was then filtered and the filtrate evaporated under reduced pressure giving an oil which on distillation gave 2-chloro-4-fluoro-3-methylaniline (72 g).
Workup
- temperaturewhole heated
- filtrationThe cooled mixture was then filtered
- customthe filtrate evaporated under reduced pressure
- customgiving an oil which
- distillationon distillation
Sources & evidence
- ORD record
- ord-3d46866fb2a540f09ab6f1323e667875
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04879423
Reaction notes
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