Sodium Hydroxide → 3,5-DIIODOANILINE

HRID 420401Notes

Reaction equation

HRID 420401 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[CH:5]=[C:6]([I:8])[CH:7]=1.O.O.Cl[Sn]Cl.[BH4-].[Na+].[OH-].[Na+]>CCO>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([I:8])[CH:7]=1)[NH2:9]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 4311764Sodium borohydrideHCID 121342563,5-diiodonitrobenzene

Product 1

HCID 121342543,5-DIIODOANILINEYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 3,5-diiodonitrobenzene (10 g, 26.7 mmol) in anhydrous EtOH (100 mL) was added SnCl2.2H2O (30 g, 133.6 mmol). The reaction mixture was brought to boil and a solution of NaBH4 (508 mg, 13.4 mmol) in EtOH (50 mL) was added slowly then stirred at reflux for 1 h. After the reaction was cooled down to 0° C., the mixture was neutralized with a solution of 3M NaOH (200 mL). The aniline derivative was extracted with chloroform, dried over Na2SO4 and evaporated under reduced pressure to afford 6.4 g of 3,5-diiodoaniline 11(70%) as a white solid. HR-ES(+): calculated for C6H5I2N [M] 345.8584, found 345.8583.

Workup

  1. temperatureat reflux for 1 h
  2. extractionThe aniline derivative was extracted with chloroform
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f5c19a811d344ebba07641504564eeb7
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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