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Water → 4-Bromo-3-methylbenzene-1,2-diamine

HRID 1411390
Notes
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Reaction equation

HRID 1411390 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 666306133-Bromo-2-methyl-6-nitroaniline

Product 1

HCID 592142734-Bromo-3-methylbenzene-1,2-diamineYield 88%

Reagents, catalysts & solvents 1

HCID 702Ethanol
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes
Solvent

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

  1. temperatureThe mixture was cooled to room temperature
  2. additionwas added
  3. extractionThe resulting mixture was extracted with CH2Cl2 (2×)
  4. dry with materialthe combined extracts were dried over Na2SO4
  5. filtrationThe drying agent was filtered off
  6. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-64b7f95f3aab454ebf12789fecc4ff63
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921514B2

Reaction notes

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