methyl 3-amino-4-(hydroxymethyl)benzoate

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

Procedure: Dissolve 3-amino-4-hydroxymethyl-benzoic acid methyl ester (step (c), 4.2 g, 23.3 mmol) in 125 mL of anhydrous CH2Cl2 and add MnO2 (20.2 g, 232.8 mmol) and stirred at RT. After 5 h, the solution was filtered through Celite and concentrated to afford the title compound as a yellow solid upon drying under vacuum. MS m/z: 180.1 (M+1). the solution was filtered through Celite concentrated

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-hydroxymethyl-3-nitro-benzoic acid methyl ester (step (b), 5.6 g, 26.5 mmol) in 60 mL EtOH/30 mL H2O was added Fe powder (7.5 g, 134.3 mmol) and NH4Cl (0.75 g, 14.0 mmol). The reaction mixture was stirred at 75° C. for 3 h, then filtered while hot through Celite. The Celite was washed with EtOAc and MeOH. The filtrate was concentrated in vacuo and partitioned between EtOAc/H2O. The EtOAc layers was dried over MgSO4 and concentrated in vacuo to give a yellow solid. MS m/z: 179.9 (M−1). filtered while hot through Celite The Celite was washed with EtOAc and MeOH The filtrate was concentrated in vacuo partitioned between EtOAc/H2O The EtOAc layers was dried over MgSO4 concentrated in vacuo to give a yellow solid