Sodium Hydroxide → 3-Methylbenzene-1,2,4,5-tetramine

HRID 1931897Notes

Reaction equation

HRID 1931897 reaction equation
Cl.Cl.Cl.Cl.[NH2:5][C:6]1[C:11]([NH2:12])=[CH:10][C:9]([NH2:13])=[C:8]([NH2:14])[C:7]=1[CH3:15].[Sn].[OH-].[Na+]>O>[NH2:5][C:6]1[C:11]([NH2:12])=[CH:10][C:9]([NH2:13])=[C:8]([NH2:14])[C:7]=1[CH3:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 86643013HCID 86643013, compound

Product 1

HCID 534720453-Methylbenzene-1,2,4,5-tetramineYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2,3,5,6-tetraaminotoluene tetrahydrochloride (TAT.4HCl)(60.59 g, 203.28 mmol) from Example 1 was added to a 1 L vessel and dissolved in deaerated water (300 g). Tin powder (0.360 g, 3.05 mmol) was added to this mixture and it was stirred for 10 minutes. NaOH (48.79 g, 1219.7 mmol) was added to 45 mL of deaerated water, allowed to cool to room temperature and then added to the stirring TAT.4HCl solution. The solution was stirred for 2 hours and free base TAT precipitated out of the solution as the solution cooled down to room temperature (18 hours). The precipitate was recovered by filtration, and washed with deaerated water (20 mL) and deaerated methanol (20 mL). This resulted in a crystalline beige solid being isolated in 82% yield (25.2 g). 1H-NMR analysis indicated TAT product purity was >99%.

Workup

  1. additionadded to the stirring TAT.4HCl solution
  2. stirringThe solution was stirred for 2 hours
  3. customfree base TAT precipitated out of the solution as the solution
  4. temperaturecooled down to room temperature (18 hours)
  5. filtrationThe precipitate was recovered by filtration
  6. washwashed with deaerated water (20 mL) and deaerated methanol (20 mL)
  7. customThis resulted in a crystalline beige solid
  8. custombeing isolated in 82% yield (25.2 g)

Sources & evidence

ORD record
ord-760a4f45a3b04f2983b6d22c71c7b4db
Source dataset
uspto-grants-2012_05
Patent number
US08188316B2

Reaction notes

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