1-Chloro-2-nitrobenzene → HCID 20037878, compound

HRID 2051678Notes

Reaction equation

HRID 2051678 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1.Cl[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[N+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 69451-Chloro-2-nitrobenzeneHCID 10340Sodium CarbonateHCID 310183-Pyridinemethanamine

Product 1

HCID 20037878HCID 20037878, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 65 parts of 3-pyridinemethanamine, 94 parts of 1-chloro-2-nitrobenzene, 80 parts of sodium carbonate and 800 parts of 1-butanol is stirred and refluxed over week-end. The reaction mixture is cooled, filtered and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding 33 parts (23%) of N-(2-nitrophenyl)-3-pyridinemethanamine.

Workup

  1. temperaturerefluxed over week-end
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. customThe residue is purified by column-chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated
  9. customThe residue is crystallized from 2,2'-oxybispropane
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-bbb5b5ad6bfe4dd79769862487e1aebc
Source dataset
uspto-grants-1980_01
Patent number
US04181802

Reaction notes

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