2,4,5-trichloroaniline

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:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,4,5-trichloroaniline (2.48 g, 12.6 mmol) in H2O (5 mL), cooled to 0° C., conc. HCl (7.5 mL) was added, and then stirred for 20 min. NaNO2 (0.87 g, 12.0 mmol) dissolved in water (5 mL), was added slowly and the reaction was continued at 0° C. for 1 h, filtered and the filtrate was used further. In another setup, ethyl 2-oxocyclohexanecarboxylate (2.0 g, 12.0 mmol) was added to 5N NaOH (0.56 g) and stirred for 16 h. The reaction mixture was cooled to 0° C., conc. HCl (1.2 mL) was added slowly, stirred for another 45 min. to obtain 2-oxocyclohexanecarboxylic acid which was added to the filtrate (prepared above) at 0° C. The resulting yellow solid precipitate was filtered, air dried to give the title compound (1.7 g, 44%) which was used in the next step without any spectroscopic analysis. was added slowly the reaction was continued at 0° C. for 1 h filtered stirred for 16 h stirred for another 45 min.

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

Procedure: A mixture of 2,4,5-trichloroaniline (39.3 g.), methane sulfonyl chloride (22.9 g.) and 100 ml. of xylene were heated together under reflux conditions for 18 hours. The mixture was then allowed to cool, which formed a brown precipitate. The product was worked up in the same manner as set forth in Example 1 to yield 24.0 g. of product, m.p. 144°-145° C. to cool which formed a brown precipitate to yield 24.0 g

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

Procedure: Compound 67 was prepared from 2,4,5-trichloroaniline, glyoxylic acid and 2,3-dihydrofuran by the automated process.

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: Compound 67 was prepared from 2,4,5-trichloroaniline, glyoxylic acid and 2,3-dihydrofuran by the automated process.

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

Procedure: Example 9 is repeated, the 3,4,5-trichloroaniline being replaced by 2,4,5-trichloroaniline and 0.5 g of the same catalyst being introduced in place of 0.1 g. After a reaction time of 10 hours under the same conditions, 3-chloroaniline is obtained with a yield of 100% for a complete conversion of the 2,4,5-trichloroaniline and of the intermediates (2,5-, 2,3- and 3,4-dichloroanilines). The degree of hydrodechlorination of the solvent is 0.09%. being introduced in place of 0.1 g

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

Procedure: A mixture of 2,4,5-trichloroaniline (39.3 g.), methane sulfonyl chloride (22.9 g.) and 100 ml. of xylene were heated together under reflux conditions for 18 hours. The mixture was then allowed to cool, which formed a brown precipitate. The product was worked up in the same manner as set forth in Example 1 to yield 24.0 g. of product, m.p. 144°-145° C. to cool which formed a brown precipitate to yield 24.0 g