Sodium Hydroxide → 6-Chloro-3-nitropyridin-2-ylamine

HRID 20087

Reaction equation

HRID 20087 reaction equation
[OH-].[NH4+:2].[OH-].[Na+].Cl[C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([Cl:15])[N:7]=1>O.C(O)C>[NH2:2][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([Cl:15])[N:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 27240356-Chloro-3-nitropyridin-2-ylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ammonium hydroxide (6.6 g, 0.124 mol) and sodium hydroxide (4.8 g, 0.120 mol) in water (45 mL) was added to 2,6-dichloro-3-nitropyridine (12.0 g, 0.62 mol) in ethanol (240 mL). The reaction was refluxed for 2 h, cooled to room temperature and filtered. The pale yellow solid was dried overnight to give the title compound. 1H NMR (500 MHz, CDCl3) δ 8.87 (d, J=9 Hz, 1H), 7.8 (br s, 1H), 6.73 (d, J=9 Hz, 1H), 5.9 (br s, 1H).

Workup

  1. temperatureThe reaction was refluxed for 2 h
  2. filtrationfiltered
  3. customThe pale yellow solid was dried overnight

Sources & evidence

ORD record
ord-9e379347c1e84156b63bf15302794ca0
Source dataset
uspto-grants-2010_06
Patent number
US07745427B2

Linked notes

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