Stannous chloride dihydrate → 3-Chloro-4-ethylaniline

A solution of 8.9 g (48 mmol) of 31 and 54.6 g (241 mmol) of SnCl2.2H2O in 100 mL of absolute alcohol was refluxed for 1 h. It was evaporated to remove most of the solvent and the residue was treated with 2N NaOH to pH=9. The mixture was filtered and the solid was washed with methanol (10 mL) and ethyl acetate (200 mL). The filtrate was separated and the aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic solution was dried (MgSO4) and evaporated to leave 7.31 g (98%) of liquid. 1H NMR (CDCl3), 1.178 (t, 3, J=7.5), 2.639 (q, 2, J=7.4), 6.532 (dd, 1, J=2.2, 8.1), 6.700 (d, 1, J=2.2), 6.996 (d, 1, J=8.2).

1. customIt was evaporated
2. customto remove most of the solvent
3. additionthe residue was treated with 2N NaOH to pH=9
4. filtrationThe mixture was filtered
5. washthe solid was washed with methanol (10 mL) and ethyl acetate (200 mL)
6. customThe filtrate was separated
7. extractionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
8. dry with materialThe combined organic solution was dried (MgSO4)
9. customevaporated

ORD record

ord-2fb376df056f44e3a691a374ab5e752e

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05977107