Methanol → 1,2-Benzenediamine, N1-ethyl-

To a solution of ethyl-(2-nitro-phenyl)-amine (12.5 g, 75 mmol) in anhydrous tetrahydrofuran (150 mL) was added sodium borohydride (5.8 g, 153 mmol), and 5% palladium on carbon (150 mg). Methanol (25 mL) was then added at room temperature under nitrogen in a dropwise manner. After addition, the reaction mixture was stirred at room temperature for about 30 minutes until the reaction was complete. The reaction mixture was then filtered through a pad of Celite. The filtrate was diluted with ethyl acetate (200 mL), washed with a saturated aqueous solution of ammonium chloride (80 mL), dried over sodium sulfite, and concentrated in vacuo to afford crude N-ethyl-benzene-1,2-diamine (8.4 g, 62 mmol) which was used in next step without further purification.

1. additionAfter addition
2. filtrationThe reaction mixture was then filtered through a pad of Celite
3. additionThe filtrate was diluted with ethyl acetate (200 mL)
4. washwashed with a saturated aqueous solution of ammonium chloride (80 mL)
5. dry with materialdried over sodium sulfite
6. concentrationconcentrated in vacuo

ORD record

ord-60baee2f88584b0390458b7d82d96349

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517899B2