Ammonium Hydroxide → 3-Amino-5-chloropyridine-2-carboxamide

HRID 1526556Notes

Reaction equation

HRID 1526556 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[OH-].[NH4+].S(S([O-])=O)([O-])=[O:16].[Na+].[Na+]>O>[NH2:10][C:4]1[C:5]([C:8]([NH2:9])=[O:16])=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 2849095-Chloro-3-nitropyridine-2-carbonitrile

Product 1

HCID 218200583-Amino-5-chloropyridine-2-carboxamideYield 58.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 5-chloro-2-cyano-3-nitropyridine (1.274 mL, 10.9 mmol) in water (22 mL) was added 28% aqueous ammonium hydroxide (3.94 mL, 28.3 mmol), and the reaction was stirred at RT for 20 minutes. Sodium hydrosulfite (2.68 mL, 32.7 mmol) was added, and the reaction mixture was stirred at RT for 70 minutes. The yellow precipitate was collected by vacuum filtration to provide the title compound (1.097 g, 6.39 mmol) as yellow solid. 1H-NMR (400 MHz, DMSO-d6): δ 7.88 (br. s, 1H), δ7.73 (s, 1H), δ7.39 (br. s, 1H), δ7.23 (s, 1H), δ7.06 (br. s, 2H). LC/MS (ESI+) m/z=172 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at RT for 70 minutes
  2. filtrationThe yellow precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-2b17b58397a14c079b7210167df35318
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

Loading…