HCID 22501934, compound → HCID 22501864, compound

Temperature

70 °C

Stannous chloride (4.75 g, 21 mmol) was added to a solution of 4-cyclopropylmethoxy-1-nitro-2-trifluoromethylbenzene (1.1 g, 4.2 mmol) in ethanol (12 mL). The reaction temperature was raised to 70° C. for 1.5 hour. The reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (20 mL). Water (15 mL) was added and sodium hydrogen carbonate was added until pH 7. The mixture was filtered and the organic phase collected. The aqueous phase was extracted with ethyl acetate (20 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (38 g) using heptane and ethyl acetate (9:1) as eluent to give 0.49 g of 4-cyclopropylmethoxy-2-trifluoromethylphenylamine.

1. concentrationThe reaction mixture was concentrated in vacuo
2. dissolutionthe residue dissolved in ethyl acetate (20 mL)
3. additionWater (15 mL) was added
4. additionsodium hydrogen carbonate was added until pH 7
5. filtrationThe mixture was filtered
6. customthe organic phase collected
7. extractionThe aqueous phase was extracted with ethyl acetate (20 mL)
8. dry with materialThe combined organic phases were dried (MgSO4)
9. concentrationconcentrated in vacuo
10. customThe residue was purified by flash chromatography (38 g)

ORD record

ord-adbf655143be41e09ae3c36ece2c02e1

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06503949B1