2-ethylcyclohexan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the solution of 2-ethyl-1-(hydroxyimino)cyclohexane (6.8 g, 48.5 mmol) in ethanol (75 mL) were added sodium pieces (about 8.0 g) in portions, and the reaction was heated to reflux at 110° C. overnight. More sodium pieces were added, and the reaction was stirred for another 6 hours. The reaction was treated with concentrated HCl (12 M, 4.0 mL) in water (25 mL). Ethanol was removed in vacuo. The aqueous layer was washed with ether (10 mL), and treated with aqueous KOH (25 mL) and extracted with ether (3×20 mL). The combined organic extracts were washed with brine (20 mL), dried over sodium sulfate, and concentrated in vacuo to give 2-ethylcyclohexylamine as an off-white oil. the reaction was heated Ethanol was removed in vacuo The aqueous layer was washed with ether (10 mL) treated with aqueous KOH (25 mL) extracted with ether (3×20 mL) The combined organic extracts were washed with brine (20 mL) dried over sodium sulfate concentrated in vacuo

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the solution of 2-ethyl-1-(hydroxyimino)cyclohexane (6.8 g, 48.5 mmol) in ethanol (75 mL) were added sodium pieces (about 8.0 g) in portions, and the reaction was heated to reflux at 110° C. overnight. More sodium pieces were added, and the reaction was stirred for another 6 hours. The reaction was treated with concentrated HCl (12 M, 4.0 mL) in water (25 mL). Ethanol was removed in vacuo. The aqueous layer was washed with ether (10 mL), and treated with aqueous KOH (25 mL) and extracted with ether (3×20 mL). The combined organic extracts were washed with brine (20 mL), dried over sodium sulfate, and concentrated in vacuo to give 2-ethylcyclohexylamine as an off-white oil. the reaction was heated Ethanol was removed in vacuo The aqueous layer was washed with ether (10 mL) treated with aqueous KOH (25 mL) extracted with ether (3×20 mL) The combined organic extracts were washed with brine (20 mL) dried over sodium sulfate concentrated in vacuo

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-ethylcyclohexylamine (0.61 mmol) in methanol was added HCl (4.0 M in dioxane, 0.152 mL), and concentrated to give a residue. Phosgene solution (20% in toluene, 6.0 mL) was added, and the reaction was heated at 110° C. overnight. Toluene and excess of phosgene were removed in vacuo to give a residue. concentrated to give a residue Toluene and excess of phosgene were removed in vacuo to give a residue

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-ethylcyclohexylamine (0.61 mmol) in methanol was added HCl (4.0 M in dioxane, 0.152 mL), and concentrated to give a residue. Phosgene solution (20% in toluene, 6.0 mL) was added, and the reaction was heated at 110° C. overnight. Toluene and excess of phosgene were removed in vacuo to give a residue. concentrated to give a residue Toluene and excess of phosgene were removed in vacuo to give a residue

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the solution of 2-ethyl-1-(hydroxyimino)cyclohexane (6.8 g, 48.5 mmol) in ethanol (75 mL) were added sodium pieces (about 8.0 g) in portions, and the reaction was heated to reflux at 110° C. overnight. More sodium pieces were added, and the reaction was stirred for another 6 hours. The reaction was treated with concentrated HCl (12 M, 4.0 mL) in water (25 mL). Ethanol was removed in vacuo. The aqueous layer was washed with ether (10 mL), and treated with aqueous KOH (25 mL) and extracted with ether (3×20 mL). The combined organic extracts were washed with brine (20 mL), dried over sodium sulfate, and concentrated in vacuo to give 2-ethylcyclohexylamine as an off-white oil. the reaction was heated Ethanol was removed in vacuo The aqueous layer was washed with ether (10 mL) treated with aqueous KOH (25 mL) extracted with ether (3×20 mL) The combined organic extracts were washed with brine (20 mL) dried over sodium sulfate concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The procedure described in Example 27 is followed, using a reaction temperature of 250° C. and a catalyst which contains 0.5% by weight of palladium on a mixture of 19.4% by weight of calcium oxide and 80.6% by weight of aluminum oxide, and starting from 2-ethylcyclohexylamine. o-Ethylaniline (boiling point=210° C.) is obtained in a yield of 95% of the theory. a reaction temperature of 250° C.

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

Procedure: The procedure described in Example 27 is followed, using a reaction temperature of 250° C. and a catalyst which contains 0.5% by weight of palladium on a mixture of 19.4% by weight of calcium oxide and 80.6% by weight of aluminum oxide, and starting from 2-ethylcyclohexylamine. o-Ethylaniline (boiling point=210° C.) is obtained in a yield of 95% of the theory. a reaction temperature of 250° C.

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

Procedure: To a solution of 0.48 g of 4-fluoro-3-nitro-benzoic acid methyl ester in 1.5 ml of abs. DMF was added 1.00 g of potassium carbonate, followed by 0.31 g of 2-ethylcyclohexylamine. After 16 h at rt, the mixture was poured into water, the pH was adjusted to 4 by the addition of 2 M aqueous hydrochloric acid, and the reaction mixture was extracted with ethyl acetate three times. The combined organic phases were washed with water, dried over sodium sulphate and concentrated to yield 0.44 g (60%) of 4-(2-Ethyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester. the reaction mixture was extracted with ethyl acetate three times The combined organic phases were washed with water dried over sodium sulphate concentrated