Potassium Hydroxide → 4-Bromo-N1-methylbenzene-1,2-diamine

HRID 1403523

Reaction equation

HRID 1403523 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([N+:10]([O-])=O)[CH:3]=1.O.O.Cl[Sn]Cl.[OH-].[K+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH:6][CH3:7])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 61436Stannous chloride dihydrateHCID 2580424-Bromo-N-methyl-2-nitroaniline

Product 1

HCID 112985934-Bromo-N1-methylbenzene-1,2-diamineYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-bromo-N-methyl-2-nitroaniline (6 g, 25.97 mmol) in ethanol (100 ml) was added SnCl2.2H2O (29 g, 128.52 mmol). The resulting solution was stirred for 3 h at 70° C., adjusted to pH 8 with potassium hydroxide (4M), extracted with ethyl acetate (2×200 ml), and the organic layers combined and concentrated under vacuum to afford 4-bromo-N1-methylbenzene-1,2-diamine as a white solid (5 g, 96%).

Workup

  1. extractionextracted with ethyl acetate (2×200 ml)
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4f18281862d04755845e3e6fb994d053
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Linked notes

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