2-methoxy-5-(methylaminomethyl)phenol

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

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

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: (4E)-6-Bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.15 g, 0.53 mmol) and 2-methoxy-5-methylaminomethyl-phenol (80 mg, 0.48 mmol) were stirred in tetrahydrofuran (10 mL) at room temperature. The reaction mixture is concentrated under reduced pressure. The solid material is then collected, washed with diethyl ether, water, and methanol, and then dried under vacuum to give (4Z)-6-bromo-4-{[(3-hydroxy-4-methoxybenzyl)(methyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione as a yellow solid (0.19 g, 95%). The reaction mixture is concentrated under reduced pressure The solid material is then collected washed with diethyl ether, water, and methanol dried under vacuum

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

Procedure: (4E)-6-Bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.15 g, 0.53 mmol) and 2-methoxy-5-methylaminomethyl-phenol (80 mg, 0.48 mmol) were stirred in tetrahydrofuran (10 mL) at room temperature. The reaction mixture is concentrated under reduced pressure. The solid material is then collected, washed with diethyl ether, water, and methanol, and then dried under vacuum to give (4Z)-6-bromo-4-{[(3-hydroxy-4-methoxybenzyl)(methyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione as a yellow solid (0.19 g, 95%). The reaction mixture is concentrated under reduced pressure The solid material is then collected washed with diethyl ether, water, and methanol dried under vacuum

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

Procedure: Methylamine (40% aqueous solution, 2.2 mL, 25 mmol) is added to a solution of 3-hydroxy-4-methoxybenzaldehyde (3.0 g, 20 mmol) in ethanol (35 mL). The resulting slurry is stirred for 30 minutes at room temperature. Then the solvents were evaporated under reduced pressure. The resulting solid is dissolved in methanol (300 mL) and sodium borohydride (0.90 g, 24 mmol) is added. The reaction mixture is stirred for 2 hours at room temperature and then concentrated under reduced pressure. The residue is partitioned between saturated aqueous potassium carbonate solution and ethyl acetate. The aqueous phase is extracted 3× with ethyl acetate, and the combined extracted were concentrated under reduced pressure to give 2-methoxy-5-methylaminomethyl-phenol as a granular white solid (2.5 g, 75%). Then the solvents were evaporated under reduced pressure The resulting solid is dissolved in methanol (300 mL) The reaction mixture is stirred for 2 hours at room temperature concentrated under reduced pressure The residue is partitioned between saturated aqueous potassium carbonate solution and ethyl acetate The aqueous phase is extracted 3× with ethyl acetate the combined extracted were concentrated under reduced pressure