1-Chloro-4-nitrobenzene → HCID 178526684, compound

HRID 726244Notes

Reaction equation

HRID 726244 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.Cl[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1>CC(O)C>[NH:6]1[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[N:8]=[CH:7]1

Participants

4

Reactant 2

HCID 74741-Chloro-4-nitrobenzeneHCID 178419017HCID 178419017, compound

Product 1

HCID 178526684HCID 178526684, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.45 g (13.1 mmol) of histamine and 2.06 g (13.1 mmol) of 1-chloro-4-nitrobenzene are brought to reflux in 20 ml of 2-propanol for 3 days. The cooled reaction mixture is filtered, evaporated and chromatographed on a first column of silica gel, using a chloroform/methanol (99/1) mixture, and then on a second column, using a chloroform/methanol (9/1) mixture. The pure fractions were evaporated and the resulting solid was treated with oxalic acid in ethanol. Addition of ether provided the title compound in the form of an oxalate salt, M.p.: 185°-186° C.

Workup

  1. customThe cooled reaction mixture
  2. filtrationis filtered
  3. customevaporated
  4. customchromatographed on a first column of silica gel
  5. customThe pure fractions were evaporated
  6. additionthe resulting solid was treated with oxalic acid in ethanol
  7. additionAddition of ether

Sources & evidence

ORD record
ord-44171b397a5a4f29a36f0f37d46f9537
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Reaction notes

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