Potassium Iodide → N-(4-fluorobenzyl)-3-nitro-2-pyridinamine

HRID 1856551Notes

Reaction equation

HRID 1856551 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.Cl[C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:12]2[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 3013927p-Fluorobenzylamine hydrochloride

Product 1

HCID 3647990N-(4-fluorobenzyl)-3-nitro-2-pyridinamineYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 9.7 parts of 4-fluorobenzenemethanamine hydrochloride, 9.4 parts of 2-chloro-3-nitropyridine, 10.6 parts of sodium carbonate, 0.1 parts of potassium iodide and 90 parts of N,N-dimethylformamide is stirred for 1 hour at 90° C. The reaction mixture is cooled and poured onto water. The precipitated product is filtered off and crystallized from 2-propanol, yielding 10.5 parts (71%) of N-(4-fluorophenylmethyl)-3-nitro-2-pyridinamine; mp. 76° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionpoured onto water
  3. filtrationThe precipitated product is filtered off
  4. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-a94ba1af8de741eba86ed6158c3f49ec
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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