Water → 4-Bromo-3-methylbenzene-1,2-diamine
Reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([C:6]([N+:9]([O-])=O)=[CH:7][CH:8]=1)[NH2:5].[Sn](Cl)Cl.O.[OH-].[Na+]>CCO>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([NH2:5])[C:6]([NH2:9])=[CH:7][CH:8]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 3-bromo-2-methyl-6-nitroaniline (0.45 g, 1.95 mmol) in EtOH (6 mL) was added tin(II) chloride (1.48 g, 7.8 mmol), and the resulting solution was stirred at 70° C. for 4 hours. The mixture was cooled to room temperature and poured into water, and 1 N aq. NaOH was added to adjust to pH>7. The resulting mixture was extracted with CH2Cl2 (2×), and the combined extracts were dried over Na2SO4. The drying agent was filtered off and solvent was removed in vacuo to give the title compound as an oil (0.34 g, 88%).
Workup
- temperatureThe mixture was cooled to room temperature
- additionwas added
- extractionThe resulting mixture was extracted with CH2Cl2 (2×)
- dry with materialthe combined extracts were dried over Na2SO4
- filtrationThe drying agent was filtered off
- customsolvent was removed in vacuo
Sources & evidence
- ORD record
- ord-77c541f335974d7a94c18a46ed4354b9
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937150B2
Reaction notes
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