Ammonia → 2-Nitro-4-[(pyridin-2-yl)methyl]aniline

HRID 2399043Notes

Reaction equation

HRID 2399043 reaction equation
[NH3:1].Cl[C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:5][C:4]=1[N+:16]([O-:18])=[O:17]>C(O)C>[NH2:1][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:5][C:4]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21432601HCID 21432601, compound

Product 1

HCID 214325902-Nitro-4-[(pyridin-2-yl)methyl]aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol(1700 ml.) was saturated with ammonia at -20° to a total volume of 3l., then 49.7 g. (0.2 mol) of 2-(4-chloro-3-nitrobenzyl)pyridine was added. The entire mixture was first autoclaved at 100° C. for 24 hours, then 185° C. for 24 hours. The resulting solution was then evaporated in vacuo to a brown solid, which was thereafter dissolved in acetone, dried with magnesium sulfate. filtered and evaporated in vacuo to a light brown solid. The resulting solid was crystallized from water using Norite to give 2-(4-amino-3-nitrobenzyl)-pyridine as yellow-orange prisms, mp. 128- 132° C. (water).

Workup

  1. wait185° C. for 24 hours
  2. customThe resulting solution was then evaporated in vacuo to a brown solid, which
  3. dissolutionwas thereafter dissolved in acetone
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to a light brown solid
  7. customThe resulting solid was crystallized from water using Norite

Sources & evidence

ORD record
ord-4fe30900edae4e13932534b43116a595
Source dataset
uspto-grants-1977_05
Patent number
US04026936

Reaction notes

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