Hydrochloric Acid → HCID 19767967, compound

HRID 1590666Notes

Reaction equation

HRID 1590666 reaction equation
[Mg].II.[CH3:4]I.[N:6]1([CH2:11][CH:12]2[C:21](=O)[C:20]3[CH:19]=[C:18]([C:23]([O:25]C(C)(C)C)=[O:24])[CH:17]=[CH:16][C:15]=3[CH2:14][CH2:13]2)[CH:10]=[CH:9][N:8]=[CH:7]1.Cl>C(OCC)C.O1CCCC1.O>[N:6]1([CH2:11][C:12]2[CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:23]([OH:25])=[O:24])=[CH:19][C:20]=3[C:21]=2[CH3:4])[CH:10]=[CH:9][N:8]=[CH:7]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 21623532HCID 21623532, compound

Product 1

HCID 19767967HCID 19767967, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of anhydrous magnesium (0.23 g) and a small crystal of iodine in anhydrous diethyl ether (3 ml) a solution of methyl iodide (1.3 g) in anhydrous diethyl ether (6 ml) is added dropwise. The mixture is refluxed for 1 hour then cooled to room temperature. To this mixture a solution of tert-butyl 5,6,7,8-tetrahydro-7-(1H-imidazol-1-ylmethyl)-8-oxo-2-naphthalenecaboxylate (1.0 g) in anhydrous tetrahydrofuran (25 ml) is added dropwise. The reaction mixture, after stirring at room temperature for 2 hours, is poured into water, neutralized with diluited hydrochloric acid and extracted with methylene chloride. The organic layer is dried over sodium sulfate and evaporated to dryness. The residue is taken up with trifluoracetic acid and refluxed for 45 minutes. The resulting solution is evaporated under reduced pressure and the residue is purified by silica gel column chromatography, eluiting with methylene chloride-methanol-acetic acid (180:20:2), to give 0.6 g of 5,6-dihydro-7-(1H-imidazol-1-ylmethyl)-8-methyl-2-naphthalenecarboxylic acid

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. customevaporated to dryness
  5. temperaturerefluxed for 45 minutes
  6. customThe resulting solution is evaporated under reduced pressure
  7. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2c99163a4bc74273b431d7c92c4a77a4
Source dataset
uspto-grants-1993_04
Patent number
US05204364

Reaction notes

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