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

HRID 637395Notes

Reaction equation

HRID 637395 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 dichloroethane. 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 dichloroethane
  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-aa1e195a8ab94017ad5e204d5c272c97
Source dataset
uspto-grants-1985_12
Patent number
US04556660

Reaction notes

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