P-Anisidine → N-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-methoxyaniline

HRID 1830283Notes

Reaction equation

HRID 1830283 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C(N([CH2:15][CH3:16])CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:26][O:27][C:28]1[C:29](=[O:51])C=[C:31]([CH2:37][C:38]2[CH:46]=[CH:45][C:41]([C:42](O)=[O:43])=[C:40]([O:47][C:48](=[O:50])[CH3:49])[CH:39]=2)[C:32](=[O:36])[C:33]=1[O:34][CH3:35]>C(Cl)Cl>[CH3:26][O:27][C:28]1[C:29](=[O:51])[C:15]([CH3:16])=[C:31]([CH2:37][C:38]2[CH:46]=[CH:45][C:41]([C:42]([NH:7][C:6]3[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[O:43])=[C:40]([O:47][C:48](=[O:50])[CH3:49])[CH:39]=2)[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 22054327HCID 22054327, compound

Product 1

HCID 22054232N-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-methoxyanilineYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Methoxyaniline (4.3 mg, 0.0349 mmol), triethylamine (5.9 mg, 0.0584 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (9.9 mg, 0.0585 mmol) were added to a methylene chloride solution (3 ml) of 4-(5,6-dimethoxy-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (11 mg, 0.0294 mmol) and the resulting solution was stirred at room temperature for 6 hours. The reaction solution was poured into ice water and then extracted with ether. 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 (hexand:ethyl acetate=1:3) to obtain the titled compound (6 mg, 0.0125 mmol, 43%).

Workup

  1. extractionextracted with ether
  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 (hexand:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-300a72b2c75a405d97107bb1014036ed
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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