Phosphorus oxychloride → 1-Ethynyl-2-methoxybenzene

HRID 1814480Notes

Reaction equation

HRID 1814480 reaction equation
COC1C=C2C([CH:7]=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[N+]([O-])=C2)=CC=1.P(Cl)(Cl)(Cl)=O>>[C:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])#[CH:7]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 225035447-Methoxy-3-(2-methoxyphenyl)isoquinoline-2-oxide

Product 1

HCID 5829121-Ethynyl-2-methoxybenzeneYield 198.7%

Procedure

7-Methoxy-3-(2-methoxyphenyl)isoquinoline-2-oxide (0.60 g) and phosphorous oxychloride (5 ml) were reacted at 110° C. for 2 hr. The reaction solution was concentrated, and to the resulting residue were added ethyl acetate and an aqueous saturated sodium bicarbonate. The resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give 0.56 g of the title compound as a white solid. (232-5) 1-(4-Ethylpiperazin-1-yl)-7-methoxy-3-(2-methoxyphenyl)isoquinoline dihydrochloride

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionto the resulting residue were added ethyl acetate
  3. washThe resulting organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-a6d960bb3d60440980807ba5e35fc6a4
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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