Ammonium Chloride → 4-Cyclopropyl-2-fluoroaniline

Temperature

90 °C

4-Cyclopropyl-2-fluoro-1-nitrobenzene (prepared as described in General Procedure 1.2C) (2.2 g, 12.14 mmol) was dissolved in 7 mL of an ethanol:THF:water 3:3:1 (v/v) mixture. To this was added ammonium chloride (1.02 g, 19.07 mmol) followed by iron powder (3.50 g, 62.7 mmol). The resulting mixture was heated in a 90° C. oil bath under a nitrogen atmosphere with rapid stirring for one hour. The reaction mixture was vacuum filtered through a sand and diatomaceous earth plug. The filtrate was concentrated in vacuo and the residue partitioned between dichloromethane and water. The organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo to provide an orange oil (1.90 g).

1. filtrationfiltered through a sand and diatomaceous earth plug
2. concentrationThe filtrate was concentrated in vacuo
3. customthe residue partitioned between dichloromethane and water
4. washThe organic phase was washed with brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo

ORD record

ord-ca8c4688b7ce4c6db046bdf55d670bc1

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08937150B2