Reaction #1509594

Reaction equation

[3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-methanol

→

title compound

Yield 77.1%

3-Methyl-5-(1-methyl-1H-tetrazol-5-yl)-phenylamine

Yield 77.1%

Solvents

MeOH

Conditions

Workup

1. 1
   Otherwas hydrogenated on a H-cube apparatus at 30° C.
2. 2
   OtherAfter reaction completion
3. 3
   Concentrationthe mixture was concentrated in vacuum
4. 4
   ExtractionThis was extracted with EtOAc
5. 5
   Otherthe organic layer was separated
6. 6
   Otherdried
7. 7
   Concentrationconcentrated in vacuum
8. 8
   OtherThe residue was purified by flash chromatography (98:2 DCM:MeOH)

Procedure

A solution of [3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-methanol (450 mg) in MeOH (20 ml) with a few drops of conc. HCl (aq) was hydrogenated on a H-cube apparatus at 30° C., and 10 bar with a flow rate of 1 mL/min using a Pd/C cartridge. After reaction completion, the mixture was concentrated in vacuum and the residue basified with a dilute K2CO3(aq). This was extracted with EtOAc and the organic layer was separated, dried and concentrated in vacuum. The residue was purified by flash chromatography (98:2 DCM:MeOH) to give the title compound (320 mg).

Source