P-Anisidine → HCID 22054218, compound

HRID 1830276Notes

Reaction equation

HRID 1830276 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:55])C=[C:31]([CH2:37][C:38]2[C:43]([C:44](O)=[O:45])=[C:42]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:41]=[CH:40][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:55])[C:15]([CH3:16])=[C:31]([CH2:37][C:38]2[C:43]([C:44]([NH:7][C:6]3[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[O:45])=[C:42]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:41]=[CH:40][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 22054289HCID 22054289, compound

Product 1

HCID 22054218HCID 22054218, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Methoxyaniline (13 mg, 0.1056 mmol), triethylamine (15 mg, 0.1485 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (24 mg, 0.1420 mmol) were added to a methylene chloride solution (3 ml) of 6-(5,6-dimethoxy-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoic acid (29 mg, 0.0687 mmol) and the resulting solution was stirred at room temperature for 3 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=1:1) to obtain the titled compound (20 mg, 0.0687 mmol, 55%).

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=1:1)

Sources & evidence

ORD record
ord-4187bf889e3847b2b45aa93a4e57d72d
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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