Water → 5-Methylisoquinoline

HRID 482460Notes

Reaction equation

HRID 482460 reaction equation
[CH3:1][Mg]I.Br[C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N:9]=[CH:10]2.O>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N:9]=[CH:10]2

Participants

6

Reactant 3

HCID 962WaterHCID 7364875-BromoisoquinolineHCID 178418373HCID 178418373, compound

Product 1

HCID 30852555-Methylisoquinoline

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A 3M solution of methyl magnesium iodide in ether (50 ml, 0.15 mol) was added dropwise to a stirred, ice-cooled solution of 5-bromoisoquinoline (21 g, 0.10 mol), obtained by the method described in J. Org. Chem., 1964, 29, 329, and [1,3-bis(diphenylphosphino)propane]nickel(II) chloride (400 mg, 0.7 mmol) in anhydrous ether and the reaction mixture heated under reflux for 5 days, allowed to cool, then poured into water (500 ml). The organic phase was separated, combined with ether extracts of the aqueous phase, washed with saturated brine, dried (MgSO4) and evaporated under reduced pressure to yield an oil, chromatography of which on silica gel, using a 5-50% ether in hexane elution gradient, provided the required product (8.4 g). Rf 0.40 (SS 8), m/e 144 (M+H)+. Found: C,79.57; H,6.26; N,8.61. C10H9N; 0.27 C4H8O2 requires C,79.70; H,6.74; N,8.39%.

Workup

  1. customobtained by the method
  2. temperatureunder reflux for 5 days
  3. temperatureto cool
  4. customThe organic phase was separated
  5. washwashed with saturated brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customto yield an oil, chromatography of which on silica gel
  9. washa 5-50% ether in hexane elution gradient

Sources & evidence

ORD record
ord-3835824b2e6e47168a3cd23986618fd5
Source dataset
uspto-grants-1998_08
Patent number
US05798352

Reaction notes

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