1-Chloro-2-nitrobenzene → 5-methyl-N-(2-nitrophenyl)-2-furanmethanamine

HRID 1534717Notes

Reaction equation

HRID 1534717 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH2:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17]>C(N(CC)CC)C>[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 27246835-Methyl-2-furylmethylamine

Product 1

HCID 141828815-methyl-N-(2-nitrophenyl)-2-furanmethanamineYield 89%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

a mixture of 40 parts of 5-methyl-2-furanmethanamine, 46 parts of 1-chloro-2-nitrobenzene and 210 parts of N,N-diethylethanamine was stirred and refluxed for 2 days. The reaction mixture was evaporated, water was added and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by filtration over silica gel using trichloromethane as eluent. The filtrate was evaporated, yielding 62 parts (89%) of 5-methyl-N-(2-nitrophenyl)-2-furanmethanamine as a residue (intermediate 2).

Workup

  1. temperaturerefluxed for 2 days
  2. customThe reaction mixture was evaporated
  3. additionwater was added
  4. extractionthe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe residue was purified by filtration over silica gel
  9. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-26e2b60f77c54e11b565ae6d7fb0cbf9
Source dataset
uspto-grants-1992_02
Patent number
USRE033833

Reaction notes

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