Ammonium Chloride → 4-Cyclopropylbenzene-1,2-diamine

4-Cyclopropyl-2-nitroaniline (178 mg, 1 mmol) was dissolved in absolute methanol (6 mL), and zinc powder (200 mg, 3.1 mmol) and ammonium chloride (800 mg, 15 mmol) were added. The mixture was stirred at room temperature for 16 hours. The mixture was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The residue was partitioned between water (30 mL) and dichloromethane (30 mL). The organic layer was separated, and the aqueous layer was extracted twice with dichloromethane (15 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give 4-cyclopropyl-benzene-1,2-diamine as a brown solid which was used without further purification (130 mg, 88%).

1. filtrationThe mixture was filtered through a pad of celite
2. concentrationthe filtrate was concentrated in vacuo
3. customThe residue was partitioned between water (30 mL) and dichloromethane (30 mL)
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted twice with dichloromethane (15 mL)
6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
7. concentrationconcentrated in vacuo

ORD record

ord-f28116a9b5b7412f9bea78a9b8681c92

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557221B2