Methanol → HCID 67373751, compound

Temperature

60 °C

To a solution of (3-nitrophenyl)(hydroxy)acetonitrile (3.5 g, 19.6 mmol) in 100 mL toluene was added sodium azide (8 g, 123 mmol) and Bu3SnCl (26 ml, 98 mmol). The mixture solution was heated at reflux for 10 hours. The solvent was removed in vacuo, the residue was dissolved in water, acidified with 1N HCl, and extracted with 3×100 mL ethyl acetate. The crude product was purified by flash chromatography on silica gel to afford 5-(3-nitrophenyl)(hydroxy)methyltetrazole (2.0 g, 9 mmol, 46%) as yellow solid. To a solution of 5-(3-nitrophenyl)(hydroxy)-methyltetrazole (1.3 g, 5.9 mmol) in 50 mL methanol was added SnCl2 (8 g, 35.4 mmol). The resulting reaction mixture was heated at 60° C. for 20 minutes. The reaction mixture was dried in vacuo, then purified directly over an ion-exchange column to afford 5-(3-aminophenyl)(hydroxy)methyltetrazole (1.0 g, 5.2 mmol, 88%), which was used directly in the next step.

1. customThe resulting reaction mixture
2. customThe reaction mixture was dried in vacuo
3. custompurified directly over an ion-exchange column

ORD record

ord-40d84368666d4b85aa766a7316199091

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07528173B2