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-a1c0d09f37b1471e9e7f5254e5ef0af2

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921514B2