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

HRID 930449Notes

Reaction equation

HRID 930449 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, 1 H), δ 7.73 (s, 1 H), δ 7.39 (br. s, 1 H), δ 7.23 (s, 1 H), δ 7.06 (br. s, 2 H). 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-ae03bad918214f11848c93b169218381
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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