6-(Azidomethyl)phenanthridine → Phenanthridin-6-ylmethanamine

HRID 718740Notes

Reaction equation

HRID 718740 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[C:7]2[C:12](=[C:13]3[C:18]=1[CH:17]=[CH:16][CH:15]=[CH:14]3)[CH:11]=[CH:10][CH:9]=[CH:8]2)=[N+]=[N-]>[Pd].CO>[CH:11]1[C:12]2[C:7](=[N:6][C:5]([CH2:4][NH2:1])=[C:18]3[C:13]=2[CH:14]=[CH:15][CH:16]=[CH:17]3)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 867124836-(Azidomethyl)phenanthridine

Product 1

HCID 11506715Phenanthridin-6-ylmethanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Activated palladium on carbon (10% w/w, 26 mg) was added to a solution of the azide 7 (258 mg, 1.10 mmol) in MeOH (40 mL). The reaction flask was purged thrice with H2 (g), pressurized to 4 bar with H2 (g), and mechanically shaken in a Parr hydrogenator for 3.5 hours. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure to yield amine 8 as a yellow oil that was used immediately in the next step without further purification.

Workup

  1. customThe reaction flask was purged thrice with H2 (g)
  2. filtrationThe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e2aa46c589aa40049ad5948319ac9293
Source dataset
uspto-grants-2015_11
Patent number
US09194802B2

Reaction notes

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