4-fluoro-7-methyl-1H-indole-2,3-dione

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Fluoro-7-methylindoline-2,3-dione (6.20 g, 34.6 mmol) in 1M NaOH (114 mL) was treated dropwise with 30% aq. H2O2 (20 mL), heated to 50° C. for 30 min, cooled to rt and filtered. The filtrate was adjusted to pH 4 with conc. HCl, cooled to 4° C. and filtered. The filter cake was dried under vacuum to provide the desired product. 1H NMR (CDCl3, 400 MHz) δ 7.15 (m, 1H), 6.40 (m, 1H), 2.15 (s, 3H). cooled to rt filtered cooled to 4° C. filtered The filter cake was dried under vacuum

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (Z)—N-(5-Fluoro-2-methylphenyl)-2-(hydroxyimino)acetamide (7.22, 37 mmol) was dissolved in neat H2SO4 (50 ml) and heated at 60° C. for 1 h. The resulting solid was collected by filtration and washed with water to yield the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.35 (bs, 1H), 7.45 (m, 1H), 6.73 (m, 1H), 2.25 (s, 3H). The resulting solid was collected by filtration washed with water

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Fluoro-7-methylindoline-2,3-dione (6.20 g, 34.6 mmol) in 1M NaOH (114 mL) was treated dropwise with 30% aq. H2O2 (20 mL), heated to 50° C. for 30 min, cooled to rt and filtered. The filtrate was adjusted to pH 4 with conc. HCl, cooled to 4° C. and filtered. The filter cake was dried under vacuum to provide the desired product. 1H NMR (CDCl3, 400 MHz) δ 7.15 (m, 1H), 6.40 (m, 1H), 2.15 (s, 3H). cooled to rt filtered cooled to 4° C. filtered The filter cake was dried under vacuum

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (Z)—N-(5-Fluoro-2-methylphenyl)-2-(hydroxyimino)acetamide (7.22, 37 mmol) was dissolved in neat H2SO4 (50 ml) and heated at 60° C. for 1 h. The resulting solid was collected by filtration and washed with water to yield the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.35 (bs, 1H), 7.45 (m, 1H), 6.73 (m, 1H), 2.25 (s, 3H). The resulting solid was collected by filtration washed with water

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

Procedure: Following the procedure as described in PREPARATION 4A, and making non-critical variations using 4-fluoro-7-methyl-1H-indole-2,3-dione (Cassebaum, J. Prakt. Chem. (1960) 12:91-92) to replace 4-chloro-1H-indole-2,3-dione, 1-(diphenylmethyl)-4-fluoro-7-methyl-1H-indole-2,3-dione was obtained (45%) as a brown solid: 1H NMR (300 MHz, CDCl3) δ7.38-7.27 (m, 11H), 6.81 (s, 1H), 6.71 (dd, J=8.3, 8.3 Hz, 1H), 2.27 (s, 3H); MS (ES+) m/z 367.7 (M+23).

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

Procedure: Following the procedure as described in PREPARATION 4A, and making non-critical variations using 4-fluoro-7-methyl-1H-indole-2,3-dione (Cassebaum, J. Prakt. Chem. (1960) 12:91-92) to replace 4-chloro-1H-indole-2,3-dione, 1-(diphenylmethyl)-4-fluoro-7-methyl-1H-indole-2,3-dione was obtained (45%) as a brown solid: 1H NMR (300 MHz, CDCl3) δ7.38-7.27 (m, 11H), 6.81 (s, 1H), 6.71 (dd, J=8.3, 8.3 Hz, 1H), 2.27 (s, 3H); MS (ES+) m/z 367.7 (M+23).

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

Procedure: Following the procedure as described in PREPARATION 4A, and making non-critical variations using 4-fluoro-7-methyl-1H-indole-2,3-dione (Cassebaum, J. Prakt. Chem. (1960) 12:91-92) to replace 4-chloro-1H-indole-2,3-dione, 1-(diphenylmethyl)-4-fluoro-7-methyl-1H-indole-2,3-dione was obtained (45%) as a brown solid: 1H NMR (300 MHz, CDCl3) δ7.38-7.27 (m, 11H), 6.81 (s, 1H), 6.71 (dd, J=8.3, 8.3 Hz, 1H), 2.27 (s, 3H); MS (ES+) m/z 367.7 (M+23).

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Fluoro-7-methylindoline-2,3-dione (6.20 g, 34.6 mmol) in 1M NaOH (114 mL) was treated dropwise with 30% aq. H2O2 (20 mL), heated to 50° C. for 30 min, cooled to rt and filtered. The filtrate was adjusted to pH 4 with conc. HCl, cooled to 4° C. and filtered. The filter cake was dried under vacuum to provide the desired product. 1H NMR (CDCl3, 400 MHz) δ 7.15 (m, 1H), 6.40 (m, 1H), 2.15 (s, 3H). cooled to rt filtered cooled to 4° C. filtered The filter cake was dried under vacuum

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (Z)—N-(5-Fluoro-2-methylphenyl)-2-(hydroxyimino)acetamide (7.22, 37 mmol) was dissolved in neat H2SO4 (50 ml) and heated at 60° C. for 1 h. The resulting solid was collected by filtration and washed with water to yield the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.35 (bs, 1H), 7.45 (m, 1H), 6.73 (m, 1H), 2.25 (s, 3H). The resulting solid was collected by filtration washed with water