Sodium Carbonate → 6-Aminonicotinamide

HRID 418157Notes

Reaction equation

HRID 418157 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.Cl.NO.C(=O)([O-])[O-:14].[Na+].[Na+]>O.C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:9])=[O:14])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 8182602-Amino-5-cyanopyridine

Product 1

HCID 95006-AminonicotinamideYield 24.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A stirred mixture of commercially available 2-amino-5-cyano-pyridine [CAS-No. 4214-73-7] (5.0 g, 42 mmol), hydroxylamine hydrochloride (17.5 g, 0.25 mol) and sodium carbonate (31.1 g, 0.29 mol) in water (95 ml) and ethanol (21 ml) was heated under reflux conditions for 6 h. The reaction mixture was poured into water (150 ml) and extracted with ethyl acetate (4×100 ml). The combined organic layers were washed with brine (150 ml), dried (MgSO4) and evaporated. The crude product was purified by column chromatography on silica gel (ethyl acetate/MeOH/NH4OH 4:1:0.5) and crystallization (ethyl acetate/MeOH/hexane) to yield 6-amino-nicotinamide (1.39 g) and the title compound (1.42 g, 22%) as an off-white solid. MS (EI) 152.1 [(M)+]; mp 300° C.

Workup

  1. temperaturewas heated under reflux conditions for 6 h
  2. extractionextracted with ethyl acetate (4×100 ml)
  3. washThe combined organic layers were washed with brine (150 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was purified by column chromatography on silica gel (ethyl acetate/MeOH/NH4OH 4:1:0.5) and crystallization (ethyl acetate/MeOH/hexane)

Sources & evidence

ORD record
ord-4aebfb57f0704ce79fb01188174778fd
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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