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

HRID 241696
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 241696
[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
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Komponenten

5

Edukt 1

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

Produkt 1

HCID 222526843-Methyl-5-(1-methyl-1H-tetrazol-5-yl)anilineAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-7febc02b807f4223bc859e8a86103a4d
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08653075B2

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