3-Aminobenzonitrile → 2-(3-Cyanophenylamino)-6-chloro-3-nitropyridine

HRID 1890665Notes

Reaction equation

HRID 1890665 reaction equation
C(=O)(O)[O-].[Na+].Cl[C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9]([Cl:16])[N:8]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[C:21]#[N:22]>C(#N)C>[Cl:16][C:9]1[N:8]=[C:7]([NH:17][C:18]2[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=2)[C:21]#[N:22])[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 167023-AminobenzonitrileHCID 852392,6-Dichloro-3-nitropyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 433302912-(3-Cyanophenylamino)-6-chloro-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

In step 1-1, sodium bicarbonate (1.68 g, 20 mmol) was added into a solution of 2,6-dichloro-3-nitropyridine (1.93 g, 10 mmol) and 3-amino benzonitrile (1.18 g, 10 mmol) in acetonitrile and the suspension was heated for 24 hours at 60° C. The mixture was filtered and washed twice with water to give 3-(6-chloro-3-nitropyridin-2-ylamino)benzonitrile (1-1) as a pale yellow solid. 1H NMR DMSO-d6 δ (ppm) 10.24 (s, 1H), 8.57 (d, 1H), 8.09 (m, 1H), 7.93 (m, 1H), 7.62 (m, 2H), 7.08 (d, 1H); m/z 357 M+1.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed twice with water

Sources & evidence

ORD record
ord-fd6592b152e342458630a0a791841d8e
Source dataset
uspto-grants-2013_08
Patent number
US08507488B2

Reaction notes

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