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

HRID 1422412Notes

Reaction equation

HRID 1422412 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-8dbd5e9be6624a71b884402429269751
Source dataset
uspto-grants-2015_01
Patent number
USRE045323E1

Reaction notes

Loading…