N-(3-aminophenyl)pentanamide

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

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 42 g of diketene were added to a mixture of 96 g of m-aminovaleranilide in 400 ml of benzene and the mixture was stirred for 16 hours at 20° C. The benzene was decanted and the residue was added to refluxing benzene. The mixture was treated with activated carbon and filtered to obtain raw m-valeramido-acetylacetanilide melting at 90° C. Crystallization from ethyl acetate yielded 34 g of pure m-valeramido-acetylacetanilide melting at 116° C. The benzene was decanted the residue was added to refluxing benzene The mixture was treated with activated carbon filtered to obtain raw m-valeramido-acetylacetanilide melting at 90° C Crystallization from ethyl acetate

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 42 g of diketene were added to a mixture of 96 g of m-aminovaleranilide in 400 ml of benzene and the mixture was stirred for 16 hours at 20° C. The benzene was decanted and the residue was added to refluxing benzene. The mixture was treated with activated carbon and filtered to obtain raw m-valeramido-acetylacetanilide melting at 90° C. Crystallization from ethyl acetate yielded 34 g of pure m-valeramido-acetylacetanilide melting at 116° C. The benzene was decanted the residue was added to refluxing benzene The mixture was treated with activated carbon filtered to obtain raw m-valeramido-acetylacetanilide melting at 90° C Crystallization from ethyl acetate

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

Procedure: A mixture of 177.6 g of m-nitrovaleranilide, 160 ml of water, 8 ml of 22° Be hydrochloric acid and 640 ml of 95% ethanol was refluxed and 480 g of iron powder were added with stirring over 30 minutes. Reflux was continued for 30 minutes with stirring and the mixture was filtered. The filtrate was concentrated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8- 2 methylene chloride-acetone mixture gave 151 g of m-aminovaleranilide with a specific rotation nD20 = 1.541. was refluxed Reflux was continued for 30 minutes with stirring the mixture was filtered The filtrate was concentrated to dryness under reduced pressure the residue was chromatographed over silica gel Elution with an 8- 2 methylene chloride-acetone mixture

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

Procedure: A mixture of 177.6 g of m-nitrovaleranilide, 160 ml of water, 8 ml of 22° Be hydrochloric acid and 640 ml of 95% ethanol was refluxed and 480 g of iron powder were added with stirring over 30 minutes. Reflux was continued for 30 minutes with stirring and the mixture was filtered. The filtrate was concentrated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8- 2 methylene chloride-acetone mixture gave 151 g of m-aminovaleranilide with a specific rotation nD20 = 1.541. was refluxed Reflux was continued for 30 minutes with stirring the mixture was filtered The filtrate was concentrated to dryness under reduced pressure the residue was chromatographed over silica gel Elution with an 8- 2 methylene chloride-acetone mixture

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

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 42 g of diketene were added to a mixture of 96 g of m-aminovaleranilide in 400 ml of benzene and the mixture was stirred for 16 hours at 20° C. The benzene was decanted and the residue was added to refluxing benzene. The mixture was treated with activated carbon and filtered to obtain raw m-valeramido-acetylacetanilide melting at 90° C. Crystallization from ethyl acetate yielded 34 g of pure m-valeramido-acetylacetanilide melting at 116° C. The benzene was decanted the residue was added to refluxing benzene The mixture was treated with activated carbon filtered to obtain raw m-valeramido-acetylacetanilide melting at 90° C Crystallization from ethyl acetate

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

Procedure: A mixture of 177.6 g of m-nitrovaleranilide, 160 ml of water, 8 ml of 22° Be hydrochloric acid and 640 ml of 95% ethanol was refluxed and 480 g of iron powder were added with stirring over 30 minutes. Reflux was continued for 30 minutes with stirring and the mixture was filtered. The filtrate was concentrated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8- 2 methylene chloride-acetone mixture gave 151 g of m-aminovaleranilide with a specific rotation nD20 = 1.541. was refluxed Reflux was continued for 30 minutes with stirring the mixture was filtered The filtrate was concentrated to dryness under reduced pressure the residue was chromatographed over silica gel Elution with an 8- 2 methylene chloride-acetone mixture