Ammonium Chloride → (1-Tosyl-1H-indol-4-YL)methanamine

HRID 475184

Reaktionsgleichung

Reaktionsgleichung von HRID 475184
[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=[N:21]O)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH4+].[Cl-]>CCO.[Zn]>[S:1]([N:11]1[C:19]2[C:14](=[C:15]([CH2:20][NH2:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 866947201-tosyl-1H-indole-4-carbaldehyde oxime

Produkt 1

HCID 67262154(1-Tosyl-1H-indol-4-YL)methanamineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 44 (620 mg, 2 mmol) in EtOH (15 mL) was added zinc powder (320 mg, 5.0 mmol) and NH4Cl (0.53 g, 10 mmol). The reaction mixture was heated at reflux overnight, filtered and the filtrate was concentrated to dryness. The residue was diluted with DCM (100 mL) and water (20 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated to afford 600 mg (100%) of (1-tosyl-1H-indol-4-yl)methanamine (46) as yellow syrup: MS (ESI) m/z=284.1 [M−15]+.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to dryness
  5. additionThe residue was diluted with DCM (100 mL) and water (20 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2ed973f2124e4f32b3d4ad3f5aa61fe1
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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