2,6-di(pentan-3-yl)aniline

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

Procedure: A mixture of 8.00 g (43 mmol) of 6-bromopyridine-2-carbaldehyde, 10.0 g (43 mmol) of 2,6-bis(1-ethylpropyl)aniline in 80 ml of ethanol was refluxed for 8 h. The obtained solution was evaporated to dryness and the residue was re-crystallized from 20 ml of methanol. Yield 11.2 g (65%) of yellow crystalline powder. Anal. calc. for C22H29BrN2: C, 65.83; H, 7.28; N, 6.98. Found: C, 66.01; H, 7.23; N, 6.90. 1H NMR (CDCl3): δ 8.21 (m, 1H, 5-H in Py), 8.15 (s, 1H, CH═N), 7.69 (m, 1H, 4-H in Py), 7.59 (m, 1H, 3-H in Py), 7.10 (m, 1H, 4-H in dipentylphenyl), 7.03-7.04 (m, 2H, 3, 5-H in dipentylphenyl), 2.48 (m, 2H, CHEt2), 1.54 (m, 8H, CH2Me), 0.74 (t, J=7.3 Hz, 12H, CH2Me). was refluxed for 8 h The obtained solution was evaporated to dryness the residue was re-crystallized from 20 ml of methanol

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

Procedure: A mixture of 8.00 g (43 mmol) of 6-bromopyridine-2-carbaldehyde, 10.0 g (43 mmol) of 2,6-bis(1-ethylpropyl)aniline in 80 ml of ethanol was refluxed for 8 h. The obtained solution was evaporated to dryness and the residue was re-crystallized from 20 ml of methanol. Yield 11.2 g (65%) of yellow crystalline powder. Anal. calc. for C22H29BrN2: C, 65.83; H, 7.28; N, 6.98. Found: C, 66.01; H, 7.23; N, 6.90. 1H NMR (CDCl3): δ 8.21 (m, 1H, 5-H in Py), 8.15 (s, 1H, CH═N), 7.69 (m, 1H, 4-H in Py), 7.59 (m, 1H, 3-H in Py), 7.10 (m, 1H, 4-H in dipentylphenyl), 7.03-7.04 (m, 2H, 3, 5-H in dipentylphenyl), 2.48 (m, 2H, CHEt2), 1.54 (m, 8H, CH2Me), 0.74 (t, J=7.3 Hz, 12H, CH2Me). was refluxed for 8 h The obtained solution was evaporated to dryness the residue was re-crystallized from 20 ml of methanol