Allyl Alcohol → 1-(Allyloxy)-6-methoxy-4-phenylisoquinoline-3-carbonitrile

HRID 639890Notes

Reaction equation

HRID 639890 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH:4]=[CH2:5].Cl[C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([C:26]#[N:27])[N:9]=1>C1COCC1>[CH2:3]([O:6][C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([C:26]#[N:27])[N:9]=1)[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 114264141-Chloro-6-methoxy-4-phenylisoquinoline-3-carbonitrile

Product 1

HCID 114384741-(Allyloxy)-6-methoxy-4-phenylisoquinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (60% in mineral oil, 14 mg) in 2 mL TEF was added 23 uL of allyl alcohol. The mixture was stirred for 15 min at room temp, then 100 mg of 1-chloro-6-methoxy-4-phenylisoquinoline-3-carbonitrile in 1.5 ml THF was added via cannula. The reaction was heated to 66 C for 16 h, then cooled to room temp, quenched with saturated aqueous NH4Cl, and partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic solution was washed once with brine, then dried (Na2SO4) and concentrated. Flash chromatography (35 g silica, 3-25% EA/hex) gave a white solid.

Workup

  1. temperatureThe reaction was heated to 66 C for 16 h
  2. temperaturecooled to room temp
  3. customquenched with saturated aqueous NH4Cl
  4. custompartitioned between EtOAc and saturated aqueous sodium bicarbonate
  5. washThe organic solution was washed once with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customFlash chromatography (35 g silica, 3-25% EA/hex) gave a white solid

Sources & evidence

ORD record
ord-5a2577f5a056426f95e206a103ca89b5
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

Loading…