Isopropylamine → N-Isopropyl-2-nitroaniline

To a solution of 1-fluoro-2-nitrobenzene (4.406 g, 31.22 mmol) in EtOH (32 mL) was added at 0° C. isopropyl amine (2.97 mL, 32.80 mmol). The mixture turned from light yellow to bright orange instantly. It was stirred overnight at RT. Another 1 eq of isopropyl amine (2.97 mL, 32.80 mmol) was added and after 3 h of stirring 2 eq of isopropyl amine were added (6 mL, 64 mmol) and the resulting solution was kept at room temperature overnight. The reaction mixture was concentrated and another equivalent of isopropyl amine was added (2.97 mL) following by EtOH (2 mL). For completion, the reaction was heated at 50° C. for 2 h. Mixture was evaporated to dryness and dissolved in EtOAc (25 mL) and the organic phase was washed with water (3*10 mL). Aqueous phase was re-extracted with EtOAc (10 mL) and the combined organics were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure to afford 5.24 g of N-isopropyl-2-nitrobenzenamine (Yield: 93%) as an orange liquid

1. additionwere added (6 mL, 64 mmol)
2. waitthe resulting solution was kept at room temperature overnight
3. concentrationThe reaction mixture was concentrated
4. additionanother equivalent of isopropyl amine was added (2.97 mL)
5. temperatureFor completion, the reaction was heated at 50° C. for 2 h
6. customMixture was evaporated to dryness
7. dissolutiondissolved in EtOAc (25 mL)
8. washthe organic phase was washed with water (3*10 mL)
9. extractionAqueous phase was re-extracted with EtOAc (10 mL)
10. washthe combined organics were washed with brine
11. dry with materialdried over Na2SO4
12. customThe solvent was evaporated under reduced pressure

ORD record

ord-0150f3d788eb4166b7041931a986ce46

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101637B2