Stannous chloride dihydrate → 4-Amino-2-ethoxybenzonitrile

Temperature

70 °C

To a suspension of 2-ethoxy-4-nitro-benzonitrile (0.49 g, 2.54 mmol) in ethanol (50 ml) is added tin (II) chloride dihydrate (2.87 g, 12.7 mmol) and the suspension is stirred at 70° C. for 2 hours and at room temperature overnight. The reaction mixture is poured onto ice-water and the pH of the solution is adjusted to pH 7-8 by addition of sodium hydrogen carbonate solution (5% solution in water). The aqueous emulsion is filtered under vacuum and the product is extracted with ethyl acetate (2×150 ml). The organic portions are combined, washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo to yield the titled product as a pale yellow solid which is used in the next step without further purification.

1. additionThe reaction mixture is poured onto ice-water
2. filtrationThe aqueous emulsion is filtered under vacuum
3. extractionthe product is extracted with ethyl acetate (2×150 ml)
4. washwashed with brine (100 ml)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo

ORD record

ord-c503b2d38a1c4c14b6eefc2ac56945bb

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470848B2