Ammonium Hydroxide → 3-Amino-6-chloropyridine-2-carboxamide

HRID 1182932Notes

Reaction equation

HRID 1182932 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-])=O)=[CH:4][CH:3]=1.[NH4+].[OH-].[O-:15]S(S([O-])=O)=O.[Na+].[Na+]>O>[NH2:10][C:5]1[C:6]([C:8]([NH2:9])=[O:15])=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Product 1

HCID 107497043-Amino-6-chloropyridine-2-carboxamideYield 70.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 6-chloro-3-nitropicolinonitrile (2.54 g, 13.8 mmol) in water (27.0 mL) was added NH4OH (5.61 mL, 36.0 mmol) at room temperature. After stirring for 20 min at room temperature, Na2S2O4 (13.7 g, 79.0 mmol) was added to the mixture. After stirring for 3 hours at room temperature, the reaction mixture was filtered, and washed with water. The filtercake was dried under vacuum to give 3-amino-6-chloropicolinamide (1.67 g, 70%) as a yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 5.36 (1H, brs), 6.00 (2H, brs), 7.00 (1H, d, J=8.8 Hz), 7.18 (1H, d, J=8.8 Hz), 7.63 (1H, brs).

Workup

  1. stirringAfter stirring for 3 hours at room temperature
  2. filtrationthe reaction mixture was filtered
  3. washwashed with water
  4. customThe filtercake was dried under vacuum

Sources & evidence

ORD record
ord-ffb9a78b6d2d4d18956d109e7492dc3d
Source dataset
uspto-grants-2014_03
Patent number
US08664230B2

Reaction notes

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