methyl 2-anilinobenzoate

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

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

Procedure: Reaction of methyl 2-(trifluoromethanesulfonyloxy)benzoate with aniline according to general procedure A provided methyl ester of 2 as a yellow oil (99% yield). 1H NMR (CDCl3, 500 MHz): δ=9.48 (s, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.22-7.40 (m, 6H), 7.10 (t, J=7.3 Hz, 1H), 6.74 (t, J=7.5 Hz, 1H), 3.91 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=169.1, 148.2, 141.0, 134.3, 131.8, 129.6, 123.8, 122.8, 117.3, 114.3, 112.2, 51.9.

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

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

Procedure: Following a procedure similar to that described in Example 1A but employing 3.1 g of 2-(1-ethyl-2-methyl-3-indolylcarbonyl)benzoic acid and 2.3 g of methyl 2-anilinobenzoate there was obtained 0.4 g of 3-(1-ethyl-2-methyl-3-indolyl)-3-[N-(2-methoxycarbonylphenyl)-N-phenylamino]phthalide, m.p. 80°-115° C. A toluene solution of the product contacted with acidic clay or phenolic resin developed a pink-colored image.

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

Procedure: Following a procedure similar to that described in Example 4 but employing 2.6 g of 2-[4-(dimethylamino)benzoyl]benzoic acid and 2.3 g of methyl 2-anilinobenzoate there was obtained 1.3 g of 3-[4-(dimethylamino)phenyl]-3-{[2-(methoxycarbonyl)phenyl]phenylamino}phthalide, m.p. 92.5°-102° C. A toluene solution of the product contacted with acidic clay developed a yellow-colored image.

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of methyl 2-aminobenzoate (7 g), iodobenzene (3.9 ml), potassium carbonate (6.4 g), and copper powder (0.46 g) was heated at 180° C. for 17 hours. The reaction solution was allowed to cool to room temperature, and ethyl acetate was added thereto. The resulting mixture was stirred and filtered with celite. The filtrate was washed with ethyl acetate and concentrated under reduced pressure. The thus-obtained residue was purified by silica gel column chromatography (developing solvent, ethyl acetate: hexane=1:30) to obtain methyl 2-phenylaminobenzoate (7.13 g; yield, 90%) as a pale yellow solid. to cool to room temperature filtered with celite The filtrate was washed with ethyl acetate concentrated under reduced pressure The thus-obtained residue was purified by silica gel column chromatography (developing solvent, ethyl acetate: hexane=1:30)

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

Procedure: Following a procedure similar to that described in Example 1A but employing 3.1 g of 2-(1-ethyl-2-methyl-3-indolylcarbonyl)benzoic acid and 2.3 g of methyl 2-anilinobenzoate there was obtained 0.4 g of 3-(1-ethyl-2-methyl-3-indolyl)-3-[N-(2-methoxycarbonylphenyl)-N-phenylamino]phthalide, m.p. 80°-115°. A toluene solution of the product contacted with acidic clay or phenolic resin developed a pink-colored image.

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

Procedure: Following a procedure similar to that described in Example 1A but employing 3.1 g of 2-(1-ethyl-2-methyl-3-indolylcarbonyl)benzoic acid and 2.3 g of methyl 2-anilinobenzoate there was obtained 0.4 g of 3-(1-ethyl-2-methyl-3-indolyl)-3-[N-(2-methoxycarbonylphenyl)-N-phenylamino]phthalide, m.p. 80°-115° C. A toluene solution of the product contacted with acidic clay or phenolic resin developed a pink-colored image.

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

Procedure: Reaction of methyl 2-(trifluoromethanesulfonyloxy)benzoate with aniline according to general procedure A provided methyl ester of 2 as a yellow oil (99% yield). 1H NMR (CDCl3, 500 MHz): δ=9.48 (s, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.22-7.40 (m, 6H), 7.10 (t, J=7.3 Hz, 1H), 6.74 (t, J=7.5 Hz, 1H), 3.91 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=169.1, 148.2, 141.0, 134.3, 131.8, 129.6, 123.8, 122.8, 117.3, 114.3, 112.2, 51.9.