Hydrochloric Acid → 3,4,5-Trichlorobenzene-1,2-diamine
Reaction equation
[N+:1]([C:4]1[C:9]([NH2:10])=[C:8]([Cl:11])[C:7]([Cl:12])=[C:6]([Cl:13])[CH:5]=1)([O-])=O.C(O)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O.[Fe]>[Cl:11][C:8]1[C:9]([NH2:10])=[C:4]([NH2:1])[CH:5]=[C:6]([Cl:13])[C:7]=1[Cl:12]Participants
Conditions
- Temperature
- 0 °C
Procedure
6-Nitro-2,3,4-trichloroaniline (17.6 g, 72.8 mmol), iron powder (140 g, 250 mmol), and ethanol (400 mL) were combined and the resulting suspension was cooled to 0° C. Concentrated hydrochloric acid (37%, 93 mL, 1.14 mol) was added dropwise over a period of 15 min by means of an addition funnel. When the addition was complete, the resulting suspension was heated to reflux for 3.5 h, after which time it was allowed to cool to room temperature and was subsequently diluted with water (2 L). The pH of the mixture was adjusted to approximately 8 by the slow addition of sodium carbonate. The product was extracted with ethyl acetate (2 L), dried over magnesium sulfate and the solvents were removed under reduced pressure by rotary evaporation. The product was further purified by silica gel chromatography using 65:35 hexane/ethyl acetate to afford 10.9 g (72%) of a tan solid; m.p. 113-115° C. Anal. Calcd for C6H5Cl3N2: C, 34.08; H, 2.38; N, 13.25. Found: C, 34.14; H, 2.41; N, 13.18.
Workup
- additionWhen the addition
- temperaturethe resulting suspension was heated
- temperatureto reflux for 3.5 h
- temperatureto cool to room temperature
- extractionThe product was extracted with ethyl acetate (2 L)
- dry with materialdried over magnesium sulfate
- customthe solvents were removed under reduced pressure by rotary evaporation
- customThe product was further purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-4221687db9134d6793c4bd3f5455e3f6
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06204249B1
Reaction notes
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