Water → 6-Amino-5-nitro-nicotinamide

HRID 53604Notes

Reaction equation

HRID 53604 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[N+:11]([O-])([O-:13])=[O:12].[K+].O.[OH-].[Na+]>C(O)(C(F)(F)F)=O>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 95006-AminonicotinamideHCID 14798Sodium HydroxideHCID 24434Potassium Nitrate

Product 1

HCID 3517576-Amino-5-nitro-nicotinamideYield 23%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 6-aminonicotinamide (524 mg, 3.82 mmol) in TFA (10 mL) was added KNO3 (524 mg, 5.18 mmol) at room temperature with stirring. The resulting solution was stirred at 80° C. for 18 h, cooled to room temperature, then cooled water (100 mL) was added (no precipitate was formed). The resulting acidic aqueous solution was basified to pH 9 with 40% aq NaOH. The precipitate was filtered, washed with cooled water (2×5 mL), and dried to give 160 mg (23%) of 65 as a yellow powder, mp 289°-90° C. 1H NMR (DMSO-d6), 7.430 (s, 1H), 8.078 (s, 1H), 8.285 (bs, 2H, easily exchanged with D20), 8.840 (s, 2H).

Workup

  1. stirringThe resulting solution was stirred at 80° C. for 18 h
  2. customwas formed)
  3. filtrationThe precipitate was filtered
  4. washwashed with cooled water (2×5 mL)
  5. customdried

Sources & evidence

ORD record
ord-205a3a0805e046b5a0a8b8b4f128dd04
Source dataset
uspto-grants-1997_04
Patent number
US05620978

Reaction notes

Loading…