2-ethylaniline

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

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

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

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

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

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

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: 5,7-Dichloro-3-methyl-1H-indazole was prepared using a procedure similar to that described in Example 98, part a and b, except starting from 2,4-dichloro-6-ethylaniline (2.9 g) that was prepared by chlorination of 6-ethylaniline (10 g) with N-chlorosuccinimide (22 g) in acetonitrile (80 mL).

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

Procedure: 1 g of 5-methyl-2-(4-nitrophenyl)-2,4-dihydro-3-pyrazolone, 190 mg of 1,3,5-triazine and 0.74 ml of 2-ethylaniline are heated under reflux in 50 ml of ethanol for 4 days. The solvent is evaporated off in vacuo, and the crude reaction product obtained in this way is purified by chromatography on silica gel with a solvent mixture consisting of dichloromethane and methanol mixed in the ratio of 97:3 as eluent. The solvent is evaporated off in vacuo the crude reaction product obtained in this way is purified by chromatography on silica gel with a solvent mixture mixed in the ratio of 97:3 as eluent

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,4-Dichloropyrimidine (596 mg, 4 mmol), 2-ethylaniline (494 ml, 4 mmol) and N,N-diisopropylethylamine (695 ml, 4 mmol) were dissolved in n-butanol (20 ml) with stirring. The reaction mixture was heated to 100° C. for 18 hours, allowed to cool to ambient temperature and evaporated onto silica (3 ml). The residue was purified by column chromatography eluting with EtOAc (0–20%): isohexane to give the title product as a colourless solid on evaporation (215 mg, 23%). NMR (CDCl3, 300 MHz): 1.20 (t, 3H), 2.61 (q, 2H), 6.26 (d, 1H), 6.80 (br, 1H) 7.31 (m, 4H), 8.04 (d, 1H); m/z: (ES−) 234.2 (MH+). to cool to ambient temperature evaporated onto silica (3 ml) The residue was purified by column chromatography eluting with EtOAc (0–20%)

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

Procedure: A solution of 2-ethylaniline (4.00 g, 33.0 mmol) in 6 N HCl (40 mL) was added (E)-but-2-enal (6.20 ml, 75.9 mmol) dropwise at reflux. The reaction was heated at reflux for 3 hours. After cooling to ambient temperature, ethyl acetate (40 mL) was added. The aqueous layer was separated, basified with ammonium hydroxide to about pH 9, and extracted with DCM (2×50 mL). The combined organic layer was dried (sodium sulfate) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (3:1 hexane/DCM) to give 8-ethyl-2-methylquinoline (3.34 g, 59.1%) as a solid. at reflux The reaction was heated at reflux for 3 hours The aqueous layer was separated extracted with DCM (2×50 mL) The combined organic layer was dried (sodium sulfate) concentrated under reduced pressure The residue was purified by flash chromatography on silica gel (3:1 hexane/DCM)