P-Anisidine → HCID 22054151, compound

HRID 1830301Notes

Reaction equation

HRID 1830301 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:26][O:27][C:28]1[C:29](=[O:52])[C:30]([CH3:51])=[C:31]([CH2:37][C:38]2[CH:39]=[CH:40][C:41]([O:47][CH:48]([CH3:50])[CH3:49])=[C:42]([CH:46]=2)[C:43](O)=[O:44])[C:32](=[O:36])[C:33]=1[O:34][CH3:35]>C(Cl)Cl>[CH3:26][O:27][C:28]1[C:29](=[O:52])[C:30]([CH3:51])=[C:31]([CH2:37][C:38]2[CH:39]=[CH:40][C:41]([O:47][CH:48]([CH3:49])[CH3:50])=[C:42]([CH:46]=2)[C:43]([NH:7][C:6]2[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:44])[C:32](=[O:36])[C:33]=1[O:34][CH3:35]

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 22054266HCID 22054266, compound

Product 1

HCID 22054151HCID 22054151, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Methoxyaniline (0.077 g, 0.626 mmol), triethylamine (0.063 g, 0.626 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.106 g, 0.626 mmol) were added to a methylene chloride solution (10 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-isopropoxybenzoic acid (0.117 g, 0.313 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (hexane:ethyl acetate=1:2) to obtain the titled compound (0.095 g, 0.198 mmol, 63%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by preparative thin-layer chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-263ba68080ef4f0385a38126d1abb61a
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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