Hydrochloric Acid → Aminostilbene
Reaction equation
[C:1]1([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[Sn]>>[C:1]1([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Procedure
At room temperature, a mixture of 12.9 g (0.057 mol) of l-phenyl-2-(2-nitro-phenyl)-ethene and 210 ml of 17% strength aqueous hydrochloric acid is admixed with 38.7 g of tin powder and slowly heated to reflux temperature. The mixture is boiled under reflux for 2 hours and then cooled to room temperature and extracted repeatedly with diethyl ether. The organic phase is concentrated under reduced pressure. The residue that remains is admixed with water, and the resulting mixture is neutralized by addition of dilute aqueous sodium hydroxide solution and then extracted repeatedly with methylene chloride. The combined organic phases are dried over sodium sulphate and subsequently concentrated under reduced pressure. The residue that remains is chromatographed over silica gel using cyclohexane:ethyl acetate=3:1. Concentration of the eluate gives 8.5 g (76.4% of theory) of 2-(2-phenylethen-1-yl)-aniline in the form of a solid substance of melting point 80° C.
Workup
- temperatureslowly heated
- temperatureto reflux temperature
- temperatureunder reflux for 2 hours
- extractionextracted repeatedly with diethyl ether
- concentrationThe organic phase is concentrated under reduced pressure
- additionthe resulting mixture is neutralized by addition of dilute aqueous sodium hydroxide solution
- extractionextracted repeatedly with methylene chloride
- dry with materialThe combined organic phases are dried over sodium sulphate
- concentrationsubsequently concentrated under reduced pressure
- customThe residue that remains is chromatographed over silica gel
Sources & evidence
- ORD record
- ord-054c80aaaeb744a9b29e666188facd4d
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06716881B2
Reaction notes
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