2-hydroxy-4-methylbenzamide

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

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 2-hydroxy-4-methyl-benzamide (15.1 g, 0.1 mol) and K2CO3 (41.7 g, 0.3 mol) in 1000 mL of acetone was heated to reflux for 1 hour before Me2SO4 was added at that temperature. The resulting mixture was refluxed overnight. The reaction mixture was then filtered and the filtrate was concentrated. The resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1) and stirred at room temperature for 3 hours. After removal of the solvent, the residue was recrystallized from EtOAc/PE to afford 102 g of 2-methoxy-4-methyl-benzamide (yield 61%). 1H NMR (400 MHz, DMSO-d6): δ 7.72 (d, J=7.6 Hz, 1H), 7.57 (br s, 1H), 7.46 (br s, 1H), 6.92 (s, 1H), 6.81 (d, J=7.6 Hz, 1H), 3.85 (s, 3H), 2.31 (s, 3H). was heated was added at that temperature The resulting mixture was refluxed overnight The reaction mixture was then filtered the filtrate was concentrated The resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1) After removal of the solvent the residue was recrystallized from EtOAc/PE

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

Procedure: A mixture of 2-hydroxy-4-methyl-benzamide (15.1 g, 0.1 mol) and K2CO3 (41.7 g, 0.3 mol) in 1000 mL of acetone was heated to reflux for 1 hour before Me2SO4 was added at that temperature. The resulting mixture was refluxed overnight. The reaction mixture was then filtered and the filtrate was concentrated. The resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1) and stirred at room temperature for 3 hours. After removal of the solvent, the residue was recrystallized from EtOAc/PE to afford 102 g of 2-methoxy-4-methyl-benzamide (yield 61%). 1H NMR (400 MHz, DMSO-d6): δ 7.72 (d, J=7.6 Hz, 1H), 7.57 (br s, 1H), 7.46 (br s, 1H), 6.92 (s, 1H), 6.81 (d, J=7.6 Hz, 1H), 3.85 (s, 3H), 2.31 (s, 3H). was heated was added at that temperature The resulting mixture was refluxed overnight The reaction mixture was then filtered the filtrate was concentrated The resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1) After removal of the solvent the residue was recrystallized from EtOAc/PE

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

Procedure: The starting-material, 4-methyl-2-propoxybenzamide, was prepared by reacting methyl 4-methyl-salicylate (25.75 g) with ethanolic ammonia to yield 4-methylsalicylamide (12.54 g) which was then reacted with bromopropane, potassium iodide and potassium carbonate in acetone.

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

Procedure: A mixture of 2-hydroxy-4-methyl-benzamide (15.1 g, 0.1 mol) and K2CO3 (41.7 g, 0.3 mol) in 1000 mL of acetone was heated to reflux for 1 hour before Me2SO4 was added at that temperature. The resulting mixture was refluxed overnight. The reaction mixture was then filtered and the filtrate was concentrated. The resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1) and stirred at room temperature for 3 hours. After removal of the solvent, the residue was recrystallized from EtOAc/PE to afford 102 g of 2-methoxy-4-methyl-benzamide (yield 61%). 1H NMR (400 MHz, DMSO-d6): δ 7.72 (d, J=7.6 Hz, 1H), 7.57 (br s, 1H), 7.46 (br s, 1H), 6.92 (s, 1 H), 6.81 (d, J=7.6 Hz, 1 H), 3.85 (s, 3H), 2.31 (s, 3H). was heated was added at that temperature The resulting mixture was refluxed overnight The reaction mixture was then filtered the filtrate was concentrated The resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1) After removal of the solvent the residue was recrystallized from EtOAc/PE

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

Procedure: The starting-material, 4-methyl-2-propoxybenzamide, was prepared by reacting methyl 4-methylsalicylate (25.75 g) with ethanolic ammonia to yield 4-methylsalicylamide (12.54 g) which was then reacted with bromopropane, potassium iodide and potassium carbonate in acetone.