3-chloro-4-ethylaniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). It was evaporated to remove most of the solvent the residue was treated with 2N NaOH The mixture was filtered the solid was washed with methanol (10 mL) and ethyl acetate (200 mL) The filtrate was separated the aqueous phase was extracted with ethyl acetate (2×50 mL) The combined organic solution was dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). It was evaporated to remove most of the solvent the residue was treated with 2N NaOH The mixture was filtered the solid was washed with methanol (10 mL) and ethyl acetate (200 mL) The filtrate was separated the aqueous phase was extracted with ethyl acetate (2×50 mL) The combined organic solution was dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). It was evaporated to remove most of the solvent the residue was treated with 2N NaOH to pH=9 The mixture was filtered the solid was washed with methanol (10 mL) and ethyl acetate (200 mL) The filtrate was separated the aqueous phase was extracted with ethyl acetate (2×50 mL) The combined organic solution was dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). It was evaporated to remove most of the solvent the residue was treated with 2N NaOH to pH=9 The mixture was filtered the solid was washed with methanol (10 mL) and ethyl acetate (200 mL) The filtrate was separated the aqueous phase was extracted with ethyl acetate (2×50 mL) The combined organic solution was dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). It was evaporated to remove most of the solvent the residue was treated with 2N NaOH to pH=9 The mixture was filtered the solid was washed with methanol (10 mL) and ethyl acetate (200 mL) The filtrate was separated the aqueous phase was extracted with ethyl acetate (2×50 mL) The combined organic solution was dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). It was evaporated to remove most of the solvent the residue was treated with 2N NaOH The mixture was filtered the solid was washed with methanol (10 mL) and ethyl acetate (200 mL) The filtrate was separated the aqueous phase was extracted with ethyl acetate (2×50 mL) The combined organic solution was dried (MgSO4) evaporated