6-Amino-5-nitro-nicotinamide → 5,6-Diaminonicotinamide
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>CO.O>[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
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
44.5 g of 6-amino-5-nitro-nicotinamide (0.24 mol; HPLC: 93% area) were suspended in methanol/water 1:1 (500 mL), 5.0 g of catalyst [Pd(4%)-Ru(1%)/C paste (62% H2O type: 485; Johnson Matthey); type: 485; Johnson Matthey] was added. Hydrogenation was carried out at 5 bar and 30° C. for 5 h. After completion the catalyst was filtered off and washed with methanol/water 1/1 (50 mL). 480 mL of the solvent was distilled off. The resulting suspension was cooled to 20° C. and filtered off. The solid was washed with methanol (20 mL) and TBME (30 mL). After drying (200-10 mbar; 40° C. bath temperature, 16 h) 27.3 g of the title compound (0.18 mol, 73%) were obtained.
Workup
- filtrationAfter completion the catalyst was filtered off
- washwashed with methanol/water 1/1 (50 mL)
- distillation480 mL of the solvent was distilled off
- filtrationfiltered off
- washThe solid was washed with methanol (20 mL) and TBME (30 mL)
Sources & evidence
- ORD record
- ord-0b5ee308417d495f88999b6e47d21374
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900324B2
Reaction notes
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