6-Amino-5-nitro-nicotinamide → 5,6-Diaminonicotinamide

HRID 53605Notes

Reaction equation

HRID 53605 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1>[Ni].CCO>[NH2:11][C:10]1[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([CH:9]=1)[C:6]([NH2:8])=[O:7]

Participants

4

Reactant 1

HCID 3517576-Amino-5-nitro-nicotinamide

Product 1

HCID 99421905,6-DiaminonicotinamideYield 86.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 65 (168 mg, 0.92 mmol), Raney Ni (about 200 mg) and EtOH (25 mL) was shaken under H2 (40 psi) for 1 h, then filtered. The filtrate was evaporated to give 121 mg (86%) of the diamine 66 as a gray powder, mp 227°-9° C.(dec.). 1H NMR (DMSO-d6), 4.747 (s, 2H), 5.890 (s, 2H), 6.867 (bs, 1H), 7.102 (s, 1H), 7.530 (bs, 1H), 7.861 (s, 1H).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-45e257035d854246b021199cbe6ebedd
Source dataset
uspto-grants-1997_04
Patent number
US05620978

Reaction notes

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