Hydroquinone → 2,5-Dimethyl-4-(2-methoxycarbonyl-ethyl-amino)-1-iodo-benzene

HRID 1017794Notes

Reaction equation

HRID 1017794 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([I:9])[C:6]([CH3:10])=[CH:5][C:3]=1[NH2:4].[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.C1(C=CC(O)=CC=1)O>>[CH3:10][C:6]1[CH:5]=[C:3]([NH:4][CH2:13][CH2:12][C:11]([O:15][CH3:16])=[O:14])[C:2]([CH3:1])=[CH:8][C:7]=1[I:9]

Participants

5

Reactant 4

HCID 785HydroquinoneHCID 7294Methyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 4770984(4-Iodo-2,5-Dimethylphenyl)Amine

Product 1

HCID 184051642,5-Dimethyl-4-(2-methoxycarbonyl-ethyl-amino)-1-iodo-benzene

Procedure

15.0 g (0.061 mol) of 2,5-dimethyl-4-iodo-aniline, 55 ml of (0.611 mol) of methyl acrylate, 6 ml of benzyltrimethyl ammonium hydroxide and 0.3 g (3 mmol) of hydroquinone are refluxed for 11 days. Then the excess acrylate is distilled off and the residue is chromatographed on silica gel, eluting with methylene chloride.

Workup

  1. distillationThen the excess acrylate is distilled off
  2. customthe residue is chromatographed on silica gel
  3. washeluting with methylene chloride

Sources & evidence

ORD record
ord-65e182c3e64e4a9287ee1088b3c7c16d
Source dataset
uspto-grants-2002_11
Patent number
US06479524B1

Reaction notes

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