N-(3-aminophenyl)propanamide

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: m-acetylaminoaniline, m-propionylaminoaniline, m-butyrylaminoaniline or m-benzoylaminoaniline;

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

Procedure: m-propionylaminoaniline, m-butyrylaminoaniline or

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

Procedure: 3-Propionylaminoaniline (16.4 parts) was reacted with n-heptyl p-toluenesulfonate (27 parts) at 100° C. for 4 hours in methyl cellosolve (200 parts) in the presence of anhydrous sodium carbonate (5.3 parts) to obtain 3-propionylamino-N-heptylaniline. Thereafter, reaction was further continued at 100° to 110° C. for 4 hours with addition of n-amyl p-toluenesulfonate (24.2 parts) and anhydrous sodium carbonate (5.3 parts) to obtain 3-propionylamino-N-n-heptyl-N-n-pentylaniline (coupling component). In the same manner as in Example 1, 2-cyano-4-nitro-6-chloroaniline was diazotized and coupled with the above coupling component to obtain 45.9 parts of a dye (7).

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

Procedure: 3-Propionylaminoaniline (16.4 parts) was reacted with n-heptyl p-toluenesulfonate (27 parts) at 100° C. for 4 hours in methyl cellosolve (200 parts) in the presence of anhydrous sodium carbonate (5.3 parts) to obtain 3-propionylamino-N-heptylaniline. Thereafter, reaction was further continued at 100° to 110° C. for 4 hours with addition of n-amyl p-toluenesulfonate (24.2 parts) and anhydrous sodium carbonate (5.3 parts) to obtain 3-propionylamino-N-n-heptyl-N-n-pentylaniline (coupling component). In the same manner as in Example 1, 2-cyano-4-nitro-6-chloroaniline was diazotized and coupled with the above coupling component to obtain 45.9 parts of a dye (7).

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

Procedure: 42 g of diketene were added to a solution of 82.1 g of m-aminopropionanilide in 400 ml of benzene and the mixture was stirred for 41/2 hours and then was vacuum filtered. The recovered precipitate was washed with benzene, then isopropyl ether and dried to obtain 118 g of m-propionamido-acetylacetanilide melting at 70° C. which was used as is for the next step. filtered The recovered precipitate was washed with benzene isopropyl ether and dried

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

Procedure: Meta-aminopropionanilide, 13.1 g. (0.08 mole) is dissolved in 200 ml. of a 50/50 v/v mixture of glacial acetic acid and saturated sodium acetate solution. To this solution is added 9.2 g. (0.088 moles) of cyclopropane carbonyl chloride. The chloride is added slowly with adequate stirring and cooling. The product, which crystallizes from the solution, is collected by filtration. The product is consecutively washed with a 5 percent solution of sodium hydroxide, a 5 percent solution of hydrochloric acid and water. After washing, the crystals are dried. There is obtained 15 g. (81 percent of theory) of the title compound, m.p. 185°-186° C. (0.08 mole) is dissolved in 200 ml To this solution is added 9.2 g cooling The product, which crystallizes from the solution is collected by filtration The product is consecutively washed with a 5 percent solution of sodium hydroxide After washing the crystals are dried There is obtained 15 g

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

Procedure: m-acetylaminoaniline, m-propionylaminoaniline, m-butyrylaminoaniline or m-benzoylaminoaniline;

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

Procedure: m-propionylaminoaniline, m-butyrylaminoaniline or

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

Procedure: 3-Propionylaminoaniline (16.4 parts) was reacted with n-heptyl p-toluenesulfonate (27 parts) at 100° C. for 4 hours in methyl cellosolve (200 parts) in the presence of anhydrous sodium carbonate (5.3 parts) to obtain 3-propionylamino-N-heptylaniline. Thereafter, reaction was further continued at 100° to 110° C. for 4 hours with addition of n-amyl p-toluenesulfonate (24.2 parts) and anhydrous sodium carbonate (5.3 parts) to obtain 3-propionylamino-N-n-heptyl-N-n-pentylaniline (coupling component). In the same manner as in Example 1, 2-cyano-4-nitro-6-chloroaniline was diazotized and coupled with the above coupling component to obtain 45.9 parts of a dye (7).

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

Procedure: 42 g of diketene were added to a solution of 82.1 g of m-aminopropionanilide in 400 ml of benzene and the mixture was stirred for 41/2 hours and then was vacuum filtered. The recovered precipitate was washed with benzene, then isopropyl ether and dried to obtain 118 g of m-propionamido-acetylacetanilide melting at 70° C. which was used as is for the next step. filtered The recovered precipitate was washed with benzene isopropyl ether and dried