Aniline → 3-nitro-N-phenylpyridin-2-amine

HRID 55525Notes

Reaction equation

HRID 55525 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.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[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 3

HCID 6115AnilineHCID 10340Sodium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 6117993-nitro-N-phenylpyridin-2-amineYield 33.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A procedure similar to that described in Preparation 66 was repeated, except that 15 g of 2-chloro-3-nitropyridine, 13.22 g of aniline and 25.07 g of sodium carbonate were reacted in 180 ml of toluene. After working up the product as described in preparation 66, the resulting crude product was purified by column chromatography through silica gel, using a 1:5 by volume mixture of ethyl acetate and hexane, to give 6.9 g of the title compound, melting at 66°-68° C.

Workup

  1. customA procedure similar to that described in Preparation 66
  2. customas described in preparation 66
  3. customthe resulting crude product was purified by column chromatography through silica gel
  4. additionby volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-ab03cc8e9cd849c6beb1ad0b306157dd
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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