4-Azidosampangine → 4-Aminosampangine

HRID 260767Notes

Reaction equation

HRID 260767 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]3[C:12]4[C:13]([C:20](=[O:21])[C:4]2=[CH:3][CH:2]=1)=[N:14][CH:15]=[C:16]([N:17]=[N+]=[N-])[C:11]=4[CH:10]=[CH:9][N:8]=3>CO>[CH:1]1[CH:6]=[C:5]2[C:7]3[C:12]4[C:13]([C:20](=[O:21])[C:4]2=[CH:3][CH:2]=1)=[N:14][CH:15]=[C:16]([NH2:17])[C:11]=4[CH:10]=[CH:9][N:8]=3

Participants

3

Reactant 1

HCID 99934324-Azidosampangine

Product 1

HCID 117767144-AminosampangineYield 48.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-azidosampangine (273 mg, 1.0 mmol) in MeOH (50 mL) was heated at reflux for 7 days. Following evaporation of the solvent, the residue was chromatographed as above to give 4-aminosampangine (23) (119 mg, 48%).

Workup

  1. temperatureat reflux for 7 days
  2. customevaporation of the solvent
  3. customthe residue was chromatographed as above

Sources & evidence

ORD record
ord-6c57e2dd4d794652b83fc028865c048c
Source dataset
uspto-grants-1996_06
Patent number
US05530004

Reaction notes

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