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

HRID 241696Notes

Reaction equation

HRID 241696 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:14]O)[CH:5]=[C:6]([C:8]2[N:12]([CH3:13])[N:11]=[N:10][N:9]=2)[CH:7]=1>CO.Cl.[Pd]>[CH3:14][C:4]1[CH:3]=[C:2]([NH2:1])[CH:7]=[C:6]([C:8]2[N:12]([CH3:13])[N:11]=[N:10][N:9]=2)[CH:5]=1

Participants

5

Reactant 1

HCID 22252683[3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-methanol

Product 1

HCID 222526843-Methyl-5-(1-methyl-1H-tetrazol-5-yl)anilineYield 77.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

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).

Workup

  1. customwas hydrogenated on a H-cube apparatus at 30° C.
  2. customAfter reaction completion
  3. concentrationthe mixture was concentrated in vacuum
  4. extractionThis was extracted with EtOAc
  5. customthe organic layer was separated
  6. customdried
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified by flash chromatography (98:2 DCM:MeOH)

Sources & evidence

ORD record
ord-7febc02b807f4223bc859e8a86103a4d
Source dataset
uspto-grants-2014_02
Patent number
US08653075B2

Reaction notes

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