Aniline → Ammonium Hydroxide

HRID 1270371Notes

Reaction equation

HRID 1270371 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCO>[NH4+:3].[OH-:9].[N+:8]([C:7]1[C:2]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 6115AnilineHCID 796132-Chloro-3-nitropyridine

Product 2

HCID 14923Ammonium HydroxideHCID 6117993-nitro-N-phenylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A stirred mixture of 2-chloro-3-nitropyridine (500 mg, 3.15 mmol) and aniline (587 mg, 6.30 mmol) in EtOH (1.5 mL) was heated in a microwave reactor for 10 min at 150° C., then concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 95:5:0.25, to provide the title compound as a solid. MS: m/z=216 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified by silica gel chromatography
  3. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-72873333e5c74e20937240810c732684
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

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