4-propoxyaniline

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

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

Procedure: A mixture of 24.5 g of 4-propoxyaniline, 19.8 g of 2,6-dichloro-3-nitrobenzoic acid, and 150 ml N,N-dimethylaniline was heated under nitrogen at 100° overnight. The cooled reaction mixture was treated with dilute base and chloroform. After the aqueous layer was washed several times with chloroform, it was treated with hydrochloric acid and the resulting orange needles were collected by filtration and washed with water to give 6-chloro-3-nitro-2-[(4-propoxyphenyl)amino]benzoic acid, mp 194°-196° C. was heated under nitrogen at 100° overnight The cooled reaction mixture was treated After the aqueous layer was washed several times with chloroform, it was treated with hydrochloric acid the resulting orange needles were collected by filtration washed with water

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

Procedure: A mixture of 24.5 g of 4-propoxyaniline, 19.8 g of 2,6-dichloro-3-nitrobenzoic acid, and 150 ml N,N-dimethylaniline was heated under nitrogen at 100° overnight. The cooled reaction mixture was treated with dilute base and chloroform. After the aqueous layer was washed several times with chloroform, it was treated with hydrochloric acid and the resulting orange needles were collected by filtration and washed with water to give 6-chloro-3-nitro-2-[(4-propoxyphenyl)amino]benzoic acid, mp 194°-196° C. was heated under nitrogen at 100° overnight The cooled reaction mixture was treated After the aqueous layer was washed several times with chloroform, it was treated with hydrochloric acid the resulting orange needles were collected by filtration washed with water

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

Procedure: The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (100 mg, 0.27 mmol) (from example 1c supra), 4-propoxy-phenylamine (61 mg, 0.41 mmol) and DIPEA (104.5 mg, 0.81 mmol) in propan-2-ol (10 mL) was stirred at room temperature for 2 h. Then water (10 mL) was added and the desired product was precipitated out, then filtrated and dried to give 98 mg of rac-6-chloro-3-(3-chloro-benzyl)-3-(4-propoxy-phenylamino)-1,3-dihydro-indol-2-one as a white solid. MS: 441 (M+H)+. the desired product was precipitated out filtrated dried

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

Procedure: The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (100 mg, 0.27 mmol) (from example 1c supra), 4-propoxy-phenylamine (61 mg, 0.41 mmol) and DIPEA (104.5 mg, 0.81 mmol) in propan-2-ol (10 mL) was stirred at room temperature for 2 h. Then water (10 mL) was added and the desired product was precipitated out, then filtrated and dried to give 98 mg of rac-6-chloro-3-(3-chloro-benzyl)-3-(4-propoxy-phenylamino)-1,3-dihydro-indol-2-one as a white solid. MS: 441 (M+H)+. the desired product was precipitated out filtrated dried

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

Procedure: A mixture of 24.5 g of 4-propoxyaniline, 19.8 g of 2,6-dichloro-3-nitrobenzoic acid, and 150 ml N,N-dimethylaniline was heated under nitrogen at 100° overnight. The cooled reaction mixture was treated with dilute base and chloroform. After the aqueous layer was washed several times with chloroform, it was treated with hydrochloric acid and the resulting orange needles were collected by filtration and washed with water to give 6-chloro-3-nitro-2-[(4-propoxyphenyl)amino]benzoic acid, mp 194°-196° C. was heated under nitrogen at 100° overnight The cooled reaction mixture was treated After the aqueous layer was washed several times with chloroform, it was treated with hydrochloric acid the resulting orange needles were collected by filtration washed with water

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

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

Procedure: 3 g of 4-n-propoxyaniline and 2.56 g of 4-(2-bromo-1-oxopropyl)-2,6-dimethylphenol were heated at 150° C. for 40 minutes in a stream of nitrogen. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was purified by silica gel column chromatography, and recrystallized from ether-hexane to give 2-(4-hydroxy-3,5-dimethylphenyl)-3-methyl-5-n-propoxyindole. the mixture was extracted with ethyl acetate The extract was purified by silica gel column chromatography recrystallized from ether-hexane

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

Procedure: 3 g of 4-n-propoxyaniline and 2.56 g of 4-(2-bromo-1-oxopropyl)-2,6-dimethylphenol were heated at 150° C. for 40 minutes in a stream of nitrogen. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was purified by silica gel column chromatography, and recrystallized from ether-hexane to give 2-(4-hydroxy-3,5-dimethylphenyl)-3-methyl-5-n-propoxyindole. the mixture was extracted with ethyl acetate The extract was purified by silica gel column chromatography recrystallized from ether-hexane

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

Procedure: Prepared as in Example 1c from 4-propoxyaniline and diethyl 2-(ethoxymethylene)malonate as a white solid (65%). 1H NMR (400 MHz, DMSO-d6) δ 0.98 (t, J=7.2 Hz, 3H), 1.25 (t, J=7.2 Hz, 3H), 1.72-1.77 (m; 2H), 3.98 (t, J=6.0 Hz, 2H), 4.16-4.21 (m, 2H), 6.97-6.99 (m, 1H), 7.53-7.56 (m, 2H), 8.47 (d, J=5.2 Hz, 1H), 12.27 (s, 1H). MS 276 (MH+).

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

Procedure: A mixture of 24.5 g of 4-propoxyaniline, 19.8 g of 2,6-dichloro-3-nitrobenzoic acid, and 150 ml N,N-dimethylaniline was heated under nitrogen at 100° overnight. The cooled reaction mixture was treated with dilute base and chloroform. After the aqueous layer was washed several times with chloroform, it was treated with hydrochloric acid and the resulting orange needles were collected by filtration and washed with water to give 6-chloro-3-nitro-2-[(4-propoxyphenyl)amino]benzoic acid, mp 194°-196° C. was heated under nitrogen at 100° overnight The cooled reaction mixture was treated After the aqueous layer was washed several times with chloroform, it was treated with hydrochloric acid the resulting orange needles were collected by filtration washed with water

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

Procedure: The method of claim 1 wherein nitrobenzene is reacted with propanol to form p-propoxyaniline.