N-(2-methoxyphenyl)formamide

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cold solution of 9.0 g of N-formyl o-anisidine in 50 mL of THF was added 66 mL of a 1M solution of LAH in THF dropwise at 0° C. After complete addition the reaction mixture was stirred at 0° C. for one h. The reaction was then quenched with ethyl acetate, then with a saturated solution of NH4Cl. The mixture was extracted with ether, the combined extracts were dried over magnesium sulfate, and the solvent was removed to give 6.0 g of product. 1H NMR (300 MHz, CDCl3) δ 2.85 (s, 3H), 3.83 (s, 3H), 4.16 (s, 1H), 6.61 (dd, 1H), 6.69 (m, 1H), 6.75 (dd, 1H), 6.87 (m, 1H). After complete addition the reaction mixture The reaction was then quenched with ethyl acetate The mixture was extracted with ether the combined extracts were dried over magnesium sulfate the solvent was removed

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

Procedure: The procedure of Example 4 was repeated using o-nitroanisole (4 mmol, 0.55 g) as starting material and vanadium(v) oxide (2.3 mg) instead of sodium molybdate dihydrate. After 2.5 h at 90-95° C. a yield of 24.8% of o-formoanisidide was obtained. o-Anisidine (62.8%) was found to be the main product. After 2.5 h at 90-95° C. a yield of 24.8% of o-formoanisidide was obtained

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cold solution of 9.0 g of N-formyl o-anisidine in 50 mL of THF was added 66 mL of a 1M solution of LAH in THF dropwise at 0° C. After complete addition the reaction mixture was stirred at 0° C. for one h. The reaction was then quenched with ethyl acetate, then with a saturated solution of NH4Cl. The mixture was extracted with ether, the combined extracts were dried over magnesium sulfate, and the solvent was removed to give 6.0 g of product. 1H NMR (300 MHz, CDCl3) δ 2.85 (s, 3H), 3.83 (s, 3H), 4.16 (s, 1H), 6.61 (dd, 1H), 6.69 (m, 1H), 6.75 (dd, 1H), 6.87 (m, 1H). After complete addition the reaction mixture The reaction was then quenched with ethyl acetate The mixture was extracted with ether the combined extracts were dried over magnesium sulfate the solvent was removed

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

Procedure: The procedure of Example 4 was repeated using o-nitroanisole (4 mmol, 0.55 g) as starting material and vanadium(v) oxide (2.3 mg) instead of sodium molybdate dihydrate. After 2.5 h at 90-95° C. a yield of 24.8% of o-formoanisidide was obtained. o-Anisidine (62.8%) was found to be the main product. After 2.5 h at 90-95° C. a yield of 24.8% of o-formoanisidide was obtained