2,3-Diaminophenol

Chemical Properties

White to beige crystalline powder

Uses

2,3-Diaminophenol was used:

• in one-pot microwave assisted synthesis of amino-1,5-benzoxazepines and hydroxyl-1,5-benzodiazepines
• in the electrosynthesis of poly(2,3-diaminophenol) via electro-oxidation
• in a synthesis of tetradentate Schiff base complexes via reaction with salicylaldehyde or 5-bromosalicylaldehyde and metals such as Mn(III), Ni(II) and Cu(II)

General Description

2,3-Diaminophenol is an aromatic diamine and forms Pd(II) and Pt(II) complexes. 2,3-Diaminophenol reacts with 2,4-pentanedione to yield the corresponding benzo[b][1,4]diazepinium salts. 2,3-Diaminophenol reacts with salicylaldehyde or 5-bromosalicylaldehyde in absolute ethanol to yield new unsymmetrical Schiff base.

Synthesis

Example 1: 11-(3-Chlorophenyl)-6-hydroxy-3,3-dimethyl-2,3,4,5,10,11-hexahydro-dibenzo[e][1,4]diaza Synthesis of 2-amino-dibenzo[e][1,4]diazepine-1-one Step 1: A mixture of 2-amino-3-nitrophenol (10.0 g, 64.9 mmol) with 10% Pd/C catalyst in ethanol (150 mL) was hydrogenated for 12 h at room temperature. Upon completion of the reaction, the reaction mixture was degassed with nitrogen followed by filtration to remove the catalyst and washing the catalyst well with ethanol. The filtrate was evaporated to afford 8.0 g (99% yield) of the target product 2,3-diaminophenol as a black solid.

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 8, p. 3309 - 3324
[2] Patent: WO2008/99019, 2008, A1. Location in patent: Page/Page column 49
[3] Patent: WO2008/99022, 2008, A1. Location in patent: Page/Page column 37-38
[4] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 380 - 396
[5] Helvetica Chimica Acta, 1951, vol. 34, p. 427,429