Water → 5-Bromobenzene-1,2,3-triamine

HRID 1051170Notes

Reaction equation

HRID 1051170 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:5]([NH2:6])=[C:4]([N+:12]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)Cl.O.[OH-].[Na+]>Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5]([NH2:6])=[C:7]([NH2:9])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 37466084-Bromo-2,6-dinitroaniline

Product 1

HCID 534141905-Bromobenzene-1,2,3-triamineYield 96.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a stirred suspension of 4-bromo-2,6-dinitroaniline (110 g, 420 mmol) in HCl conc (2200 mL) at −20° C. was added tin(II)chloride dihydrate (568 g, 2519 mmol, 6 eq) in one portion under cooling. After stirring overnight ar rt, water (1000 mL) was added to the suspension, and the pH was adjusted to 10 using sodium hydroxide (50% aqueous solution). After extraction with ethyl acetate (3×2000 mL), the organic phase was washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated in vaccuo to yield 81.5 g 5-bromobenzene-1,2,3-triamine (96.1%).

Workup

  1. temperatureunder cooling
  2. extractionAfter extraction with ethyl acetate (3×2000 mL)
  3. washthe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vaccuo

Sources & evidence

ORD record
ord-4a98c957f285411eb05efbd3aaf98d26
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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