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

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Reaction Steps

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%.

Provenance & Evidence